Updated on 2025/11/11

写真a

 
SUGA Seiji
 
Organization
Administrative Center Director
Position
Director
External link

Degree

  • Doctor (Ssience) ( 1995.3   Nagoya University )

Research Interests

  • フロー合成

  • 有機合成化学

  • 有機電気化学

Research Areas

  • Nanotechnology/Materials / Synthetic organic chemistry

Education

  • Nagoya University   大学院理学研究科   化学専攻

    1986.4 - 1994.3

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  • Nagoya University   理学部   化学科

    1982.4 - 1986.3

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Research History

  • Okayama University   Faculty of Environmental, Life, Natural Science and Technology

    2023.4

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  • Okayama University   Executive Director for Academic Affairs

    2023.4

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  • Okayama University   Dean of School of Engineering

    2021.4 - 2023.3

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  • Okayama University

    2019.4 - 2021.3

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  • Okayama University

    2017.4 - 2019.3

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  • Okayama University   The Graduate School of Natural Science and Technology   Professor

    2008.10 - 2023.3

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  • Kyoto University   Graduate School of Engineering Department of Synthetic Chemistry and Biological Chemistry   Associate Professor

    2007.4 - 2008.9

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  • Kyoto University   Graduate School of Engineering Department of Synthetic Chemistry and Biological Chemistry   Associate Professor (as old post name)

    2003.7 - 2007.3

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  • Kyoto University   Graduate School of Engineering Department of Synthetic Chemistry and Biological Chemistry   Lecturer

    1999.2 - 2003.6

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  • Kyoto University   Graduate School of Engineering Department of Synthetic Chemistry and Biological Chemistry   Research Assistant

    1996.9 - 1999.3

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  • University of Oxford

    1995.3 - 1996.9

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  • Nagoya University   Graduate School of Science   Special researcher of the Japan Society for the Promotion of Science

    1991.4 - 1993.3

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Papers

  • Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers Reviewed

    Yuta Niki, Koichi Mitsudo, Eisuke Sato, Seiji Suga

    Organic Letters   2024.12

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.orglett.4c03928

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  • SNAr Hexafluoroisopropoxylation of Electron-rich Aryl Fluoride with a Catalytic Electrical Input Reviewed

    Eisuke Sato, Tomohiro Nakahama, Koichi Mitsudo, Seiji Suga

    Chemistry Letters   2024.10

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Oxford University Press (OUP)  

    Abstract

    Anodic oxidation-promoted SNAr reactions of electron-rich aryl fluoride were developed. The anodic oxidation of 4-fluoroanisole in hexafluoroisopropyl alcohol (HFIP) with K2CO3 led to SNAr-type hexafluoroisopropoxylation, and the reaction was completed with a catalytic electrical input. The results of cyclic voltammetry suggest that the radical cation of 4-fluoroanisole, which would react with the alkoxide of HFIP, is generated. Electron transfer between the intermediate and the starting material constructs the catalytic cycle, and the elimination of fluoride from the Meisenheimer complex produces the desired compound.

    DOI: 10.1093/chemle/upae196

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  • Electrocatalytic Hydrogenation of Pyridines and Other Nitrogen-Containing Aromatic Compounds Reviewed

    Naoki Shida, Yugo Shimizu, Akizumi Yonezawa, Juri Harada, Yuka Furutani, Yusuke Muto, Ryo Kurihara, Junko N. Kondo, Eisuke Sato, Koichi Mitsudo, Seiji Suga, Shoji Iguchi, Kazuhide Kamiya, Mahito Atobe

    Journal of the American Chemical Society   146 ( 44 )   30212 - 30221   2024.10

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/jacs.4c09107

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  • Electrochemical synthesis of heterocyclic compounds via carbon–heteroatom bond formation: direct and indirect electrolysis Invited Reviewed

    Yasuyuki Okumura, Eisuke Sato, Koichi Mitsudo, Seiji Suga

    Chemistry Letters   53 ( 8 )   upae146   2024.7

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Oxford University Press (OUP)  

    Abstract

    Electrochemical organic synthesis has attracted attention as an environmentally friendly method for constructing heterocyclic compounds via carbon–heteroatom bond formation. Herein, we describe the representative examples of electrochemical reactions to produce heterocycles and discuss them according to whether they involve direct or indirect electrolysis.

    DOI: 10.1093/chemle/upae146

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    Other Link: https://academic.oup.com/chemlett/article-pdf/53/8/upae146/58904624/upae146.pdf

  • Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor Invited Reviewed

    Koichi Mitsudo, Atsushi Osaki, Haruka Inoue, Eisuke Sato, Naoki Shida, Mahito Atobe, Seiji Suga

    Beilstein Journal of Organic Chemistry   20   1560 - 1571   2024.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Beilstein Institut  

    An electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines using a proton-exchange membrane (PEM) reactor was developed. Cyanoarenes were then reduced to the corresponding benzylamines at room temperature in the presence of ethyl phosphate. The reduction of nitroarenes proceeded at room temperature, and a variety of anilines were obtained. The quinoline reduction was efficiently promoted by adding a catalytic amount of p-toluenesulfonic acid (PTSA) or pyridinium p-toluenesulfonate (PPTS). Pyridine was also reduced to piperidine in the presence of PTSA.

    DOI: 10.3762/bjoc.20.139

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    Other Link: https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-20-139.pdf

  • Sequential Paired Electrochemical Transformation of Styrene Oxide via Anodic Meinwald Rearrangement and Cathodic Nitro­methylation in an Electrochemical Flow Reactor with Catalytic Electrical Input

    Eisuke Sato, Kanon Nagamine, Chika Sasaki, Shumpei Kunimoto, Koichi Mitsudo, Seiji Suga

    Synthesis   56 ( 16 )   2507 - 2512   2024.4

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag KG  

    Abstract

    Paired electrosynthesis, which utilize both anodic and cathodic events in electrolysis, enables attractive transformations with higher current efficiency than conventional electrosynthesis. The electrochemical flow technique has been widely employed to ensure stable reaction conditions and mitigate issues stemming from mass transfer. In this study, the electrochemical Meinwald rearrangement of styrene oxides was investigated, yielding aldehydes as intermediates, followed by the nitromethylation of aldehydes to produce β-nitro alcohols. These reactions were achieved with catalytic electrical input, enabling the conversion of various styrene oxides into the corresponding β-nitro alcohols.

    DOI: 10.1055/a-2309-6737

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  • [1,2]-Retro-Brook rearrangement induced by electrochemical reduction of silyl enolates

    Ban Kinoshita, Saki Maejima, Yuta Niki, Koichi Mitsudo, Seiji Suga, Hideki Yorimitsu

    Bulletin of the Chemical Society of Japan   97 ( 4 )   uoae038   2024.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Oxford University Press (OUP)  

    Abstract

    Electrochemical reduction of the trimethylsilyl enolates of alkyl aryl ketones induces retro-Brook rearrangement to provide 1-aryl-1-trimethylsilylalkan-1-ols. The transformation proceeds through a sequence of 1) single-electron reduction of the silyl enolate, 2) protonation with a phenol, 3) another single-electron reduction to form a siloxy-substituted benzylic anion, and 4) the pivotal retro-Brook rearrangement.

    DOI: 10.1093/bulcsj/uoae038

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    Other Link: https://academic.oup.com/bcsj/article-pdf/97/4/uoae038/57322484/uoae038.pdf

  • Terrein Exhibits Anti-tumor Activity by Suppressing Angiogenin Expression in Malignant Melanoma Cells. Reviewed International journal

    Taira Hirose, Yuki Kunisada, Koichi Kadoya, Hiroki Mandai, Yumi Sakamoto, Kyoichi Obata, Kisho Ono, Hiroaki Takakura, Kazuhiro Omori, Shogo Takashiba, Seiji Suga, Soichiro Ibaragi

    Cancer genomics & proteomics   21 ( 5 )   464 - 473   2024

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    Language:English   Publishing type:Research paper (scientific journal)  

    BACKGROUND/AIM: Malignant melanoma is a tumor with a poor prognosis that can metastasize distally at an early stage. Terrein, a metabolite produced by Aspergillus terreus, suppresses the expression of angiogenin, an angiogenic factor. However, the pharmacological effects of natural terrein have not been elucidated, because only a small amount of terrein can be extracted from large fungal cultures. In this study, we investigated the antineoplastic effects of terrein on human malignant melanoma cells and its underlying mechanisms. MATERIALS AND METHODS: Human malignant melanoma cell lines were cultured in the presence of terrein and analyzed. Angiogenin production was evaluated using ELISA. Ribosome biosynthesis was evaluated using silver staining of the nucleolar organizer region. Intracellular signaling pathways were analyzed using western blotting. Malignant melanoma cells were transplanted subcutaneously into the backs of nude mice. The tumors were removed at 5 weeks and analyzed histopathologically. RESULTS: Terrein inhibited angiogenin expression, proliferation, migration, invasion, and ribosome biosynthesis in malignant melanoma cells. Terrein was shown to inhibit tumor growth and angiogenesis in animal models. CONCLUSION: This study demonstrated that terrein has anti-tumor effects against malignant melanoma. Furthermore, chemically synthesized non-natural terrein can be mass-produced and serve as a novel potential anti-tumor drug candidate.

    DOI: 10.21873/cgp.20464

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  • Alkynylation of Aldehydes Initiated by Cathodic Reduction Invited Reviewed

    Eisuke Sato, Mayu Fujii, Koichi Mitsudo, Seiji Suga

    ChemElectroChem   11 ( 1 )   2023.12

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    Abstract

    Alkynylation of aldehydes initiated by cathodic reduction was performed. The cathodic alkynylation required only a semi‐catalytic amount of electricity to consume the starting material completely. Cyclic voltammetry and some control experiments suggest that the electron‐generated base derived from the cathodic reduction of benzaldehyde promotes alkynylation.

    DOI: 10.1002/celc.202300499

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  • Electrochemical Synthesis of Dibenzothiophene S,S-Dioxides from Biaryl Sulfonyl Hydrazides Invited Reviewed

    Yasuyuki OKUMURA, Eisuke SATO, Koichi MITSUDO, Seiji SUGA

    Electrochemistry   91 ( 11 )   112007   2023.11

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Electrochemical Society of Japan  

    DOI: 10.5796/electrochemistry.23-67078

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  • Cathodic N–O Bond Cleavage of N-Alkoxy Amide Invited Reviewed

    Eisuke SATO, Sayaka OGITA, Koichi MITSUDO, Seiji SUGA

    Electrochemistry   91 ( 11 )   112005   2023.11

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Electrochemical Society of Japan  

    DOI: 10.5796/electrochemistry.23-67079

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  • Electrochemical Coupling Reactions Using Non‐Transition Metal Mediators: Recent Advances Invited Reviewed

    Koichi Mitsudo, Yasuyuki Okumura, Eisuke Sato, Seiji Suga

    European Journal of Organic Chemistry   26 ( 47 )   e202300835   2023.11

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    Abstract

    Indirect electrolysis method using appropriate mediators enables numerous chemical reactions. The general principles of mediators were described herein with a particular focus on non‐transition metal mediators. Recent representative examples of bond formation reactions by indirect electrolysis are summarized and discussed here.

    DOI: 10.1002/ejoc.202300835

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  • Anodic Dehydrogenative Aromatization of Tetrahydrocarbazoles Leading to Carbazoles Reviewed

    Eisuke Sato, Ayaka Yukiue, Koichi Mitsudo, Seiji Suga

    Organic Letters   25 ( 28 )   5339 - 5344   2023.7

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.3c01914

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  • Electrochemical Synthesis of Sultone Derivatives via Dehydrogenative C-O Bond Formation. Reviewed International journal

    Koichi Mitsudo, Yasuyuki Okumura, Kotaro Yohena, Yuji Kurimoto, Eisuke Sato, Seiji Suga

    Organic letters   25 ( 19 )   3476 - 3481   2023.5

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    Electrochemical dehydrogenative C-O bond formation for the synthesis of sultones was achieved. In the presence of K2CO3 and H2O, constant current electrolysis of [1,1'-biphenyl]-2-sulfonyl chloride afforded an aryl-fused sultone quantitatively. Under the optimized conditions, a variety of sultone derivatives were obtained. Control experiments suggest that the electrochemical oxidation of the sulfonates generated in situ would afford sulfo radical intermediates.

    DOI: 10.1021/acs.orglett.3c01062

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  • The Fungal Metabolite (+)-Terrein Abrogates Inflammatory Bone Resorption via the Suppression of TNF-α Production in a Ligature-Induced Periodontitis Mouse Model Reviewed

    Hidefumi Sako, Kazuhiro Omori, Masaaki Nakayama, Hiroki Mandai, Hidetaka Ideguchi, Saki Yoshimura-Nakagawa, Kyosuke Sakaida, Chiaki Nagata-Kamei, Hiroya Kobayashi, Satoki Ishii, Mitsuaki Ono, Soichiro Ibaragi, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba

    Journal of Fungi   9 ( 3 )   314 - 314   2023.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:MDPI AG  

    Current periodontal treatment focuses on the mechanical removal of the source of infection, such as bacteria and their products, and there is no approach to control the host inflammatory response that leads to tissue destruction. In order to control periodontal inflammation, we have previously reported the optimization of (+)-terrein synthesis methods and the inhibitory effect of (+)-terrein on osteoclast differentiation in vitro. However, the pharmacological effect of (+)-terrein in vivo in the periodontitis model is still unknown. In this study, we investigated the effect of synthetic (+)-terrein on inflammatory bone resorption using a ligature-induced periodontitis mouse model. Synthetic (+)-terrein (30 mg/kg) was administered intraperitoneally twice a week to the mouse periodontitis model. The control group was treated with phosphate buffer. One to two weeks after the induction of periodontitis, the periodontal tissues were harvested for radiological evaluation (micro-CT), histological evaluation (HE staining and TRAP staining), and the evaluation of inflammatory cytokine production in the periodontal tissues and serum (quantitative reverse-transcription PCR, ELISA). The synthetic (+)-terrein-treated group suppressed alveolar bone resorption and the number of osteoclasts in the periodontal tissues compared to the control group (p < 0.05). In addition, synthetic (+)-terrein significantly suppressed both mRNA expression of TNF-α in the periodontal tissues and the serum concentration of TNF-α (both p < 0.05). In conclusion, we have demonstrated that synthetic (+)-terrein abrogates alveolar bone resorption via the suppression of TNF-α production and osteoclast differentiation in vivo. Therefore, we could expect potential clinical effects when using (+)-terrein on inflammatory bone resorption, including periodontitis.

    DOI: 10.3390/jof9030314

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  • Electrochemical Cross-Coupling Reactions between Arylboronic Esters and Aryllithiums Using NaBr as a Halogen Mediator Invited Reviewed

    Koichi Mitsudo, Seiji Suga, Keisuke Shigemori, Taro Shibata, Hiroki Mandai, Eisuke Sato

    Synthesis   55 ( 18 )   2999 - 3004   2023.2

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag KG  

    Abstract

    An electrochemical cross-coupling reaction between arylboronic esters and aryllithiums was developed. The presence of Br– in the electrolyte was found to be essential for the reaction. NaBr was chosen as the electrolyte for its inexpensiveness and abundance, and also acted as a halogen mediator. The reaction proceeded under mild conditions to afford biaryls.

    DOI: 10.1055/a-2034-9821

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  • Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions Reviewed

    Eisuke Sato, Gaku Tachiwaki, Mayu Fujii, Koichi Mitsudo, Takashi Washio, Shinobu Takizawa, Seiji Suga

    Organic Process Research & Development   28 ( 5 )   1422 - 1429   2023.1

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    DOI: 10.1021/acs.oprd.2c00267

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  • Electrochemical Synthesis of Dibenzothiophenes via Intramolecular C–S Cyclization with a Halogen Mediator Reviewed

    Koichi Mitsudo, Yuri Tachibana, Eisuke Sato, Seiji Suga

    Organic Letters   24 ( 46 )   8547 - 8552   2022.11

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.2c03574

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  • A Facile Access to Spirooxindoles by Halogen-mediated Electrochemical Semi-pinacol Rearrangement Reviewed

    Eisuke Sato, Sae Kangawa, Koichi Mitsudo, Seiji Suga

    Chemistry Letters   51 ( 11 )   1067 - 1069   2022.11

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.220368

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  • Electrochemical hydrogenation of enones using a proton-exchange membrane reactor: selectivity and utility Invited Reviewed

    Koichi Mitsudo, Haruka Inoue, Yuta Niki, Eisuke Sato, Seiji Suga

    Beilstein Journal of Organic Chemistry   18   1055 - 1061   2022.8

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Beilstein Institut  

    Electrochemical hydrogenation of enones using a proton-exchange membrane reactor is described. The reduction of enones proceeded smoothly under mild conditions to afford ketones or alcohols. The reaction occurred chemoselectively with the use of different cathode catalysts (Pd/C or Ir/C).

    DOI: 10.3762/bjoc.18.107

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    Other Link: https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-18-107.pdf

  • Electro-oxidative Trimerization of 1,2-Dimethoxybenzene: Reductive Workup Strategy and Alternating Current Electrolysis to Peel off the Precipitated Radical Cation Ion Pair Reviewed

    Eisuke Sato, Yuta Niki, Koichi Mitsudo, Seiji Suga

    Chemistry Letters   51 ( 6 )   629 - 632   2022.6

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.220112

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  • Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis Reviewed

    Eisuke Sato, Mayu Fujii, Hiroki Tanaka, Koichi Mitsudo, Masaru Kondo, Shinobu Takizawa, Hiroaki Sasai, Takeshi Washio, Kazunori Ishikawa, Seiji Suga

    The Journal of Organic Chemistry   86 ( 22 )   16035 - 16044   2021.8

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.joc.1c01242

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  • The Fungal Metabolite (+)-Terrein Abrogates Ovariectomy-Induced Bone Loss and Receptor Activator of Nuclear Factor-κB Ligand–Induced Osteoclastogenesis by Suppressing Protein Kinase-C α/βII Phosphorylation Reviewed

    Kyosuke Sakaida, Kazuhiro Omori, Masaaki Nakayama, Hiroki Mandai, Saki Nakagawa, Hidefumi Sako, Chiaki Kamei, Satoshi Yamamoto, Hiroya Kobayashi, Satoki Ishii, Mitsuaki Ono, Soichiro Ibaragi, Keisuke Yamashiro, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba

    Frontiers in Pharmacology   12   674366   2021.6

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Frontiers Media SA  

    Osteoporosis is a common disease characterized by a systemic impairment of bone mass and microarchitecture that results in fragility fractures. Severe bone loss due to osteoporosis triggers pathological fractures and consequently decreases the daily life activity and quality of life. Therefore, prevention of osteoporosis has become an important issue to be addressed. We have reported that the fungal secondary metabolite (+)-terrein (TER), a natural compound derived from Aspergillus terreus, has shown receptor activator of nuclear factor-κB ligand (RANKL)–induced osteoclast differentiation by suppressing nuclear factor of activated T-cell 1 (NFATc1) expression, a master regulator of osteoclastogenesis. TER has been shown to possess extensive biological and pharmacological benefits; however, its effects on bone metabolism remain unclear. In this study, we investigated the effects of TER on the femoral bone metabolism using a mouse-ovariectomized osteoporosis model (OVX mice) and then on RANKL signal transduction using mouse bone marrow macrophages (mBMMs). In vivo administration of TER significantly improved bone density, bone mass, and trabecular number in OVX mice (p < 0.01). In addition, TER suppressed TRAP and cathepsin-K expression in the tissue sections of OVX mice (p < 0.01). In an in vitro study, TER suppressed RANKL-induced phosphorylation of PKCα/βII, which is involved in the expression of NFATc1 (p < 0.05). The PKC inhibitor, GF109203X, also inhibited RANKL-induced osteoclastogenesis in mBMMs as well as TER. In addition, TER suppressed the expression of osteoclastogenesis-related genes, such as Ocstamp, Dcstamp, Calcr, Atp6v0d2, Oscar, and Itgb3 (p < 0.01). These results provide promising evidence for the potential therapeutic application of TER as a novel treatment compound against osteoporosis.

    DOI: 10.3389/fphar.2021.674366

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  • Cu-Catalyzed Dehydrogenative C–O Cyclization for the Synthesis of Furan-Fused Thienoacenes Reviewed

    Koichi Mitsudo, Yoshiaki Kobashi, Kaito Nakata, Yuji Kurimoto, Eisuke Sato, Hiroki Mandai, Seiji Suga

    Organic Letters   23 ( 11 )   4322 - 4326   2021.5

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.1c01256

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  • Electrosynthesis of Phosphacycles via Dehydrogenative C–P Bond Formation Using DABCO as a Mediator Reviewed

    Yuji Kurimoto, Jun Yamashita, Koichi Mitsudo, Eisuke Sato, Seiji Suga

    Organic Letters   23 ( 8 )   3120 - 3124   2021.4

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.1c00807

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  • Acylative Desymmetrization of Cyclic meso-1,3-Diols by Chiral DMAP Derivatives Reviewed

    Hiroki Mandai, Tsubasa Hironaka, Koichi Mitsudo, Seiji Suga

    Chemistry Letters   50 ( 3 )   471 - 474   2021.3

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.200809

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  • Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles Reviewed

    Hiroki Mandai, Ryuhei Shiomoto, Kazuki Fujii, Koichi Mitsudo, Seiji Suga

    Organic Letters   23 ( 4 )   1169 - 1174   2021.2

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.orglett.0c03956

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  • Acylative desymmetrization of glycerol derivatives by chiral dmap derivatives Reviewed

    Hiroki Mandai, Kosuke Ashihara, Koichi Mitsudo, Seiji Suga

    Heterocycles   102 ( 6 )   1083 - 1090   2021

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.3987/COM-21-14433

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  • Synthesis, optical and electrochemical properties of 4,4′-bibenzo[c]thiophene derivatives Reviewed

    Kotaro Obayashi, Keiichi Imato, Satoshi Aoyama, Toshiaki Enoki, Seiji Akiyama, Mio Ishida, Seiji Suga, Koichi Mitsudo, Yousuke Ooyama

    RSC Advances   11 ( 31 )   18870 - 18880   2021

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>4,4′-Bibenzo[<italic>c</italic>]thiophene <bold>4,4′-BBT</bold> and its silyl-substituted derivatives <bold>1,1′-Si-4,4′-BBT</bold> and <bold>1,1′,3,3′-Si-4,4′-BBT</bold> have been designed and developed as new π-building blocks.</p>

    DOI: 10.1039/d1ra01189h

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  • Synthesis of 9-Substituted Fluorenols and Heteroring-fused Analogues by Intramolecular C–H Functionalization Reviewed

    Yuji Kurimoto, Koichi Mitsudo, Seiji Suga

    Chemistry Letters   50 ( 2 )   378 - 381   2020.12

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Oxford University Press (OUP)  

    Abstract

    A method for the selective synthesis of 9-substituted fluorenols (FOLs) was developed by suppressing intermolecular cyclization and promoting intramolecular C–H functionalization. This protocol was applied to the synthesis of heteroring-fused FOLs. Further, the obtained FOLs were converted to fulvenes by dehydration.

    DOI: 10.1246/cl.200807

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  • Integrated Synthesis of Thienyl Thioethers and Thieno[3,2-b]thiophenes via 1-Benzothiophen-3(2H)-ones Invited Reviewed

    Koichi Mitsudo, Nanae Habara, Yoshiaki Kobashi, Yuji Kurimoto, Hiroki Mandai, Seiji Suga

    Synlett   31 ( 19 )   1947 - 1952   2020.12

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-0040-1707280

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  • The fungal metabolite (+)-terrein abrogates osteoclast differentiation via suppression of the RANKL signaling pathway through NFATc1 Reviewed

    Saki Nakagawa, Kazuhiro Omori, Masaaki Nakayama, Hiroki Mandai, Satoshi Yamamoto, Hiroya Kobayashi, Hidefumi Sako, Kyosuke Sakaida, Hiroshi Yoshimura, Satoki Ishii, Soichiro Ibaragi, Kimito Hirai, Keisuke Yamashiro, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba

    International Immunopharmacology   83   106429   2020.6

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    DOI: 10.1016/j.intimp.2020.106429

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  • Electrochemical Synthesis of Thienoacene Derivatives: Transition‐Metal‐Free Dehydrogenative C−S Coupling Promoted by a Halogen Mediator Reviewed

    Koichi Mitsudo, Ren Matsuo, Toki Yonezawa, Haruka Inoue, Hiroki Mandai, Seiji Suga

    Angewandte Chemie   132 ( 20 )   7877 - 7881   2020.5

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/ange.202001149

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  • Electrochemical Synthesis of Thienoacene Derivatives: Transition-Metal-Free Dehydrogenative C-S Coupling Promoted by a Halogen Mediator Reviewed

    Koichi Mitsudo, Ren Matsuo, Toki Yonezawa, Haruka Inoue, Hiroki Mandai, Seiji Suga

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   59 ( 20 )   7803 - 7807   2020.5

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    DOI: 10.1002/anie.202001149

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  • Preface

    Seiji Suga

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   78 ( 4 )   291 - 291   2020.4

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  • 1,10-Phenanthroline- or Electron-Promoted Cyanation of Aryl Iodides Invited Reviewed

    Koichi Mitsudo, Kazuki Yoshioka, Takayuki Hirata, Hiroki Mandai, Koji Midorikawa, Seiji Suga

    Synlett   30 ( 10 )   1209 - 1214   2019.6

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    DOI: 10.1055/s-0037-1611793

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  • Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel-Crafts C-H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives Reviewed

    Keisuke Shigemori, Momoka Watanabe, Julie Kong, Koichi Mitsudo, Atsushi Wakamiya, Hiroki Mandai, Seiji Suga

    Organic Letters   21 ( 7 )   2171 - 2175   2019.4

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    DOI: 10.1021/acs.orglett.9b00485

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  • Enantioselective Acyl Migration Reactions of Furanyl Carbonates with Chiral DMAP Derivatives Reviewed

    Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai, Toshinobu Korenaga, Seiji Suga

    CHEMISTRY-A EUROPEAN JOURNAL   25 ( 9 )   2208 - 2212   2019.2

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    DOI: 10.1002/chem.201806050

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  • Enantioselective Desymmetrization of 1,3-Diols by a Chiral DMAP Derivative Reviewed

    Hiroki Mandai, Kosuke Ashihara, Koichi Mitsudo, Seiji Suga

    Chemistry Letters   47 ( 11 )   1360 - 1363   2018.11

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    DOI: 10.1246/cl.180697

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  • Fungal metabolite (+)-terrein suppresses IL-6/sIL-6R-induced CSF1 secretion by inhibiting JAK1 phosphorylation in human gingival fibroblasts Reviewed

    Satoshi Yamamoto, Kazuhiro Omori, Hiroki Mandai, Masaaki Nakayama, Saki Nakagawa, Hiroya Kobayashi, Tadashi Kunimine, Hiroshi Yoshimura, Kyosuke Sakaida, Hidefumi Sako, Soichiro Ibaragi, Tadashi Yamamoto, Hiroshi Maeda, Seiji Suga, Shogo Takashiba

    Heliyon   4 ( 11 )   e00979   2018.11

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    DOI: 10.1016/j.heliyon.2018.e00979

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  • Synthesis and Properties of Dithieno-Fused 1,4-Azaborine Derivatives Reviewed

    Koichi Mitsudo, Keisuke Shigemori, Hiroki Mandai, Atsushi Wakamiya, Seiji Suga

    Organic Letters   20 ( 22 )   7336 - 7340   2018.11

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    DOI: 10.1021/acs.orglett.8b03316

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  • Efficient Synthesis and Properties of [1]Benzothieno[3,2-b]thieno[2,3-d]furans and [1]Benzothieno[3,2-b]thieno[2,3-d]thiophenes Reviewed

    Yuji Kurimoto, Koichi Mitsudo, Hiroki Mandai, Atsushi Wakamiya, Yasujiro Murata, Hiroki Mori, Yasushi Nishihara, Seiji Suga

    ASIAN JOURNAL OF ORGANIC CHEMISTRY   7 ( 8 )   1635 - 1641   2018.8

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    DOI: 10.1002/ajoc.201800270

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  • Cu/Fe/O=PPh3-Catalyzed Etherification for the Synthesis of Aryl 3-Benzo[b]thienyl Ethers Reviewed

    Koichi Mitsudo, Takuya Asada, Tomohiro Inada, Yuji Kurimoto, Hiroki Mandai, Seiji Suga

    Chemistry Letters   47 ( 8 )   1044 - 1047   2018.8

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    DOI: 10.1246/cl.180425

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  • Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1 '-Binaphthyl Unit: Importance of Amide Groups Reviewed

    Hiroki Mandai, Kohei Hongo, Takuma Fujiwara, Kazuki Fujii, Koichi Mitsudo, Seiji Suga

    Organic Letters   20 ( 16 )   4811 - 4814   2018.8

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    DOI: 10.1021/acs.orglett.8b01960

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  • SYNTHESIS OF OXAZOLINES FROM N-ALLYLAMIDES USING AN ELECTROCHEMICALLY GENERATED ArS(ArSSAr)(+) POOL Reviewed

    Yu Miyamoto, Naoya Mitani, Rina Yanagi, Shigenori Kashimura, Seiji Suga, Jun-ichi Yoshida, Kouichi Matsumoto

    HETEROCYCLES   96 ( 8 )   1373 - 1382   2018.8

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    DOI: 10.3987/COM-18-13942

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  • Miniaturization and Combinatorial Approach in Organic Electrochemistry Invited Reviewed

    Koichi Mitsudo, Yuji Kurimoto, Kazuki Yoshioka, Seiji Suga

    CHEMICAL REVIEWS   118 ( 12 )   5985 - 5999   2018.6

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    DOI: 10.1021/acs.chemrev.7b00532

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  • Recent topics in enantioselective acyl transfer reactions with dialkylaminopyridine-based nucleophilic catalysts Invited Reviewed

    Hiroki Mandai, Kazuki Fujii, Seiji Suga

    TETRAHEDRON LETTERS   59 ( 19 )   1787 - 1803   2018.5

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    DOI: 10.1016/j.tetlet.2018.03.016

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  • Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations Invited Reviewed

    Koichi Mitsudo, Junya Yamamoto, Tomoya Akagi, Atsuhiro Yamashita, Masahiro Haisa, Kazuki Yoshioka, Hiroki Mandai, Koji Ueoka, Christian Hempel, Jun-ichi Yoshida, Seiji Suga

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   14   1192 - 1202   2018.5

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    DOI: 10.3762/bjoc.14.100

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  • Combinatorial electrochemistry for organic synthesis Invited Reviewed

    Koichi Mitsudo, Yuji Kurimoto, Kazuki Yoshioka, Seiji Suga

    CURRENT OPINION IN ELECTROCHEMISTRY   8   8 - 13   2018.3

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    DOI: 10.1016/j.coelec.2017.10.026

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  • Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts Reviewed

    Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai, Seiji Suga

    ADVANCED SYNTHESIS & CATALYSIS   359 ( 16 )   2778 - 2788   2017.8

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    DOI: 10.1002/adsc.201700057

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  • Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1'-Binaphthyl Unit: Importance of the Hydroxy Groups Reviewed

    Hiroki Mandai, Hiroshi Yasuhara, Kazuki Fujii, Yukihito Shimomura, Koichi Mitsudo, Seiji Suga

    JOURNAL OF ORGANIC CHEMISTRY   82 ( 13 )   6846 - 6856   2017.7

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    DOI: 10.1021/acs.joc.7b00992

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  • Development of Efficient and Effective Rate Acceleration Systems in Organocatalysis

    Hiroki Mandai, Kazuki Fujii, Seiji Suga

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   75 ( 6 )   632 - 649   2017.6

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    DOI: 10.5059/yukigoseikyokaishi.75.632

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  • Synthesis of 3-Benzo[b]thienyl 3-Thienyl Ether via an Addition-Elimination Reaction and Its Transformation to an Oxygen-Fused Dithiophene Skeleton: Synthesis and Properties of Benzodithienofuran and Its pi-Extended Derivatives Reviewed

    Koichi Mitsudo, Yuji Kurimoto, Hiroki Mandai, Seiji Suga

    Organic Letters   19 ( 11 )   2821 - 2824   2017.6

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    DOI: 10.1021/acs.orglett.7b00969

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  • Rh-Catalyzed Dehydrogenative Cyclization Leading to Benzosilolothiophene Derivatives via Si-H/C-H Bond Cleavage Reviewed

    Koichi Mitsudo, Seiichi Tanaka, Ryota Isobuchi, Tomohiro Inada, Hiroki Mandai, Toshinobu Korenaga, Atsushi Wakamiya, Yasujiro Murata, Seiji Suga

    Organic Letters   19 ( 10 )   2564 - 2567   2017.5

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    DOI: 10.1021/acs.orglett.7b00878

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  • Magnetic Attachment of Lipase Immobilized on Bacteriogenic Iron Oxide Inside a Microtube Reactor for the Kinetic Resolution of Secondary Alcohols Reviewed

    Kyoko Mandai, Takehiro Fukuda, Yuki Miyazaki, Hideki Hashimoto, Hiroki Mandai, Tadashi Ema, Jun Takada, Seiji Suga

    Synlett   28 ( 7 )   805 - 810   2017.4

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    DOI: 10.1055/s-0036-1589953

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  • AN INTRAMOLECULAR NUCLEOPHILE-CATALYZED ALDOL-LACTONIZATION (NCAL) REACTION OF S-ARYL-(E)-6-OXOHEX-2-ENETHIOATE WITH N,N-4-DIMETHYLAMINOPYRIDINE N-OXIDE Reviewed

    Hiroki Mandai, Keita Shimowaki, Kohei Hongo, Koichi Mitsudo, Seiji Suga

    HETEROCYCLES   94 ( 3 )   492 - 502   2017.3

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    DOI: 10.3987/COM-16-13614

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  • Facile Synthesis of Naphthothiophenone Derivatives and Anthradithiophenedione via Friedel-Crafts Acylation and Their Fundamental Properties

    Koichi Mitsudo, Takashi Murakami, Takuya Shibasaki, Tomohiro Inada, Hiroki Mandai, Hiromi Ota, Seiji Suga

    SYNLETT   27 ( 16 )   2327 - 2332   2016.10

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    DOI: 10.1055/s-0035-1562470

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  • Kinetic Resolution of Secondary Carbinols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1 '- Binaphthyl Unit: Hydrogen Bonding Affects Catalytic Activity and Enantioselectivity

    Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai, Seiji Suga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   89 ( 9 )   1081 - 1092   2016.9

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    DOI: 10.1246/bcsj.20160135

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  • Synthetic Terrein Inhibits Progression of Head and Neck Cancer by Suppressing Angiogenin Production

    Akane Shibata, Soichiro Ibaragi, Hiroki Mandai, Toki Tsumura, Koji Kishimoto, Tatsuo Okui, Nur Mohammad Monsur Hassan, Tsuyoshi Shimo, Kazuhiro Omori, Guo-Fu Hu, Shogo Takashiba, Seiji Suga, Akira Sasaki

    ANTICANCER RESEARCH   36 ( 5 )   2161 - 2168   2016.5

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  • Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions

    Hiroki Mandai, Kazuki Fujii, Hiroshi Yasuhara, Kenko Abe, Koichi Mitsudo, Toshinobu Korenaga, Seiji Suga

    NATURE COMMUNICATIONS   7   2016.4

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    DOI: 10.1038/ncomms11297

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  • Facile Synthesis of 1,4-Bis(diaryl)-1,3-butadiynes Bearing Two Amino Moieties by Electrochemical Reaction-Site Switching, and Their Solvatochromic Fluorescence

    Natsuyo Kamimoto, Nariaki Nakamura, Akina Tsutsumi, Hiroki Mandai, Koichi Mitsudo, Atsushi Wakamiya, Yasujiro Murata, Jun-ya Hasegawa, Seiji Suga

    ASIAN JOURNAL OF ORGANIC CHEMISTRY   5 ( 3 )   373 - 379   2016.3

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    DOI: 10.1002/ajoc.201500502

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  • Bacteriogenic iron oxide as an effective catalyst for Baeyer-Villiger oxidation with molecular oxygen and benzaldehyde

    Kyoko Mandai, Minae Hanata, Koichi Mitsudo, Hiroki Mandai, Seiji Suga, Hideki Hashimoto, Jun Takada

    TETRAHEDRON   71 ( 50 )   9403 - 9407   2015.12

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    DOI: 10.1016/j.tet.2015.10.057

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  • Synthesis and Properties of Ethene-Bridged Terthiophenes

    Koichi Mitsudo, Hidehiko Sato, Arata Yamasaki, Natsuyo Kamimoto, Jun Goto, Hirold Mandai, Seiji Suga

    ORGANIC LETTERS   17 ( 19 )   4858 - 4861   2015.10

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    DOI: 10.1021/acs.orglett.5b02417

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  • Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N,N-4-(Dimethylamino)pyridine Derivatives

    Hiroki Mandai, Takuma Fujiwara, Katsuaki Noda, Kazuki Fujii, Koichi Mitsudo, Toshinobu Korenaga, Seiji Suga

    ORGANIC LETTERS   17 ( 18 )   4436 - 4439   2015.9

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    DOI: 10.1021/acs.orglett.5b02089

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  • Palladium-Catalyzed Domino CH/NH Functionalization: An Efficient Approach to Nitrogen-Bridged Heteroacenes

    Natsuyo Kamimoto, Dieter Schollmeyer, Koichi Mitsudo, Seiji Suga, Siegfried R. Waldvogel

    CHEMISTRY-A EUROPEAN JOURNAL   21 ( 22 )   8257 - 8261   2015.5

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    DOI: 10.1002/chem.201500897

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  • Development of Cross-Coupling Reactions Including Electro-oxidative Processes and Their Applications to the Synthesis of pi-Extended Compounds

    Koichi Mitsudo, Hideo Tanaka, Seiji Suga

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   73 ( 2 )   171 - 180   2015.2

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  • Organoelemental compounds

    Jun-Ichi Yoshida, Toshiki Nokami, Seiji Suga

    Organic Electrochemistry, Fifth Edition: Revised and Expanded   1357 - 1392   2015.1

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  • Low temperature in situ Raman spectroscopy of an electro-generated arylbis(arylthio)sulfonium ion

    Kouichi Matsumoto, Yu Miyamoto, Kazuaki Shimada, Yusuke Morisawa, Hendrik Zipse, Seiji Suga, Jun-ichi Yoshida, Shigenori Kashimura, Tomonari Wakabayashi

    CHEMICAL COMMUNICATIONS   51 ( 66 )   13106 - 13109   2015

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    DOI: 10.1039/c5cc03585f

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  • 4.電解発生カチオン性パラジウム触媒を用いる有機合成

    光藤 耕一, 菅 誠治

    Electrochemistry   83 ( 6 )   477 - 482   2015

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    DOI: 10.5796/electrochemistry.83.477

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  • Preparation and Capacitive Performance of Mesoporous Carbon with Short Time CO2 Activation

    Akinori Muto, Keiichiro Itano, Shohei Wada, Shunsuke Ohtani, Hayato Tokumoto, Seiji Suga

    ELECTROCHEMISTRY   82 ( 12 )   1067 - 1071   2014.12

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    DOI: 10.5796/electrochemistry.82.1067

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  • Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts

    Hiroki Mandai, Kazuhiro Omori, Daisuke Yamamoto, Toki Tsumura, Kyouta Murota, Satoshi Yamamoto, Koichi Mitsudo, Soichiro Ibaragi, Akira Sasaki, Hiroshi Maeda, Shogo Takashiba, Seiji Suga

    BIOORGANIC & MEDICINAL CHEMISTRY   22 ( 19 )   5338 - 5344   2014.10

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    DOI: 10.1016/j.bmc.2014.07.047

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  • An Efficient Petasis Boronic-Mannich Reaction of Chiral Lactol Derivatives Prepared from D-Araboascorbic Acid

    Hiroki Mandai, Hiroshi Yamada, Keita Shimowaki, Koichi Mitsudo, Seiji Suga

    SYNTHESIS-STUTTGART   46 ( 19 )   2672 - 2681   2014.10

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    DOI: 10.1055/s-0034-1378900

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  • Remarkable Enhancement of the Rate of the Intramolecular MoritaBaylis- Hillman Reaction by the Combination of a Nucleophilic Catalyst and 1,3-Diphenyl-2-thiourea

    Hiroki Mandai, Keita Shimowaki, Koichi Mitsudo, Seiji Suga

    ASIAN JOURNAL OF ORGANIC CHEMISTRY   3 ( 4 )   437 - 441   2014.4

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    DOI: 10.1002/ajoc.201402001

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  • Addition of N-Acyliminium Ion Pools to Alkenes Having a Nucleophilic Moiety: Integration of Intermolecular and Intramolecular Reactions

    Yosuke Ashikari, Yohei Kiuchi, Tomoya Takeuchi, Koji Ueoka, Seiji Suga, Jun-ichi Yoshida

    CHEMISTRY LETTERS   43 ( 2 )   210 - 212   2014.2

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    DOI: 10.1246/cl.130947

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  • Electrogenerated Acid (EGA)-catalyzed Addition of Diaryl Disulfides to Carbon-Carbon Multiple Bonds

    Kouichi Matsumoto, Hayato Shimazaki, Tomonari Sanada, Kazuaki Shimada, Shino Hagiwara, Seiji Suga, Shigenori Kashimura, Jun-ichi Yoshida

    CHEMISTRY LETTERS   42 ( 8 )   843 - 845   2013.8

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    DOI: 10.1246/cl.130255

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  • Electro-reductive Halogen-Deuterium Exchange and Methylation of Aryl Halides in Acetonitrile

    Koichi Mitsudo, Takahiro Okada, Shuichi Shimohara, Hiroki Mandai, Seiji Suga

    ELECTROCHEMISTRY   81 ( 5 )   362 - 364   2013.5

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    DOI: 10.5796/electrochemistry.81.362

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  • Recyclable Palladium Catalyst in PEG/CH3CN Biphasic System for Electro-oxidative Wacker-type Reaction

    Koichi Mitsudo, Satoshi Fukunaga, Tomoya Fujita, Hiroki Mandai, Seiji Suga, Hideo Tanaka

    ELECTROCHEMISTRY   81 ( 5 )   347 - 349   2013.5

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    DOI: 10.5796/electrochemistry.81.347

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  • The Addition of ArSSAr to Alkenes: The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)(+)

    Kouichi Matsumoto, Tomonari Sanada, Hayato Shimazaki, Kazuaki Shimada, Shino Hagiwara, Shunsuke Fujie, Yosuke Ashikari, Seiji Suga, Shigenori Kashimura, Jun-ichi Yoshida

    ASIAN JOURNAL OF ORGANIC CHEMISTRY   2 ( 4 )   325 - 329   2013.4

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    DOI: 10.1002/ajoc.201300017

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  • Synthesis of Hexa(furan-2-yl)benzenes and Their pi-Extended Derivatives

    Koichi Mitsudo, Jyunji Harada, Yo Tanaka, Hiroki Mandai, Chie Nishioka, Hideo Tanaka, Atsushi Wakamiya, Yasujiro Murata, Seiji Suga

    JOURNAL OF ORGANIC CHEMISTRY   78 ( 6 )   2763 - 2768   2013.3

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    DOI: 10.1021/jo302652r

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  • KINETIC RESOLUTION OF SECONDARY ALCOHOLS BY CHIRAL DMAP DERIVATIVES PREPARED BY THE UGI MULTICOMPONENT REACTION

    Hiroki Mandai, Shunsuke Irie, Masaru Akehi, Kazunobu Yuri, Masaaki Yoden, Koichi Mitsudo, Seiji Suga

    HETEROCYCLES   87 ( 2 )   329 - 340   2013.2

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    DOI: 10.3987/COM-12-12624

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  • Electro-reductive cyclization of aryl halides promoted by fluorene derivatives

    Koichi Mitsudo, Yumiko Nakagawa, Jun-ichi Mizukawa, Hideo Tanaka, Ryoichi Akaba, Takahiro Okada, Seiji Suga

    ELECTROCHIMICA ACTA   82   444 - 449   2012.11

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    DOI: 10.1016/j.electacta.2012.03.130

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  • Kinetic Resolution of Secondary Alcohols by the Combination of a Chiral Bronsted Acid, DABCO, and Acetyl Chloride

    Hiroki Mandai, Kyouta Murota, Koichi Mitsudo, Seiji Suga

    ORGANIC LETTERS   14 ( 13 )   3486 - 3489   2012.7

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    DOI: 10.1021/ol301373x

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  • STUDIES ON THE PETASIS REACTION OF 2-PYRIDINECARBALDEHYDE DERIVATIVES AND ITS PRODUCTS

    Hiroki Mandai, Kyouta Murota, Seiji Suga

    HETEROCYCLES   85 ( 7 )   1655 - +   2012.7

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    DOI: 10.3987/COM-12-12500

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  • Synthesis of Nitrogen-Bridged Terthiophenes by Tandem Buchwald-Hartwig Coupling and Their Properties

    Koichi Mitsudo, Shuichi Shimohara, Jun Mizoguchi, Hiroki Mandai, Seiji Suga

    ORGANIC LETTERS   14 ( 11 )   2702 - 2705   2012.6

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    DOI: 10.1021/ol300887t

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  • Electrophilic substitution reactions using an electrogenerated ArS(ArSSAr)(+) cation pool as an ArS+ equivalent

    Kouichi Matsumoto, Yuki Kozuki, Yosuke Ashikari, Seiji Suga, Shigenori Kashimura, Jun-ichi Yoshida

    TETRAHEDRON LETTERS   53 ( 15 )   1916 - 1919   2012.4

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    DOI: 10.1016/j.tetlet.2012.01.131

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  • Site-selective sequential coupling reactions controlled by "Electrochemical Reaction Site Switching": a straightforward approach to 1,4-bis(diaryl)buta-1,3-diynes

    Koichi Mitsudo, Natsuyo Kamimoto, Hiroki Murakami, Hiroki Mandai, Atsushi Wakamiya, Yasujiro Murata, Seiji Suga

    ORGANIC & BIOMOLECULAR CHEMISTRY   10 ( 48 )   9562 - 9569   2012

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    DOI: 10.1039/c2ob26567b

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  • Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions

    Hiroki Mandai, Shunsuke Irie, Koichi Mitsudo, Seiji Suga

    MOLECULES   16 ( 10 )   8815 - 8832   2011.10

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  • TRPA1 underlies a sensing mechanism for O-2

    Nobuaki Takahashi, Tomoyuki Kuwaki, Shigeki Kiyonaka, Tomohiro Numata, Daisuke Kozai, Yusuke Mizuno, Shinichiro Yamamoto, Shinji Naito, Ellen Knevels, Peter Carmeliet, Toru Oga, Shuji Kaneko, Seiji Suga, Toshiki Nokami, Jun-ichi Yoshida, Yasuo Mori

    NATURE CHEMICAL BIOLOGY   7 ( 10 )   701 - 711   2011.10

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  • Kumada-Tamao-Corriu Coupling Using N-Heterocyclic Carbene Ligands Bearing Pyridyl and Ethylenedioxyl Moieties

    Koichi Mitsudo, Yuta Doi, Syunsuke Sakamoto, Hiroki Murakami, Hiroki Mandai, Seiji Suga

    CHEMISTRY LETTERS   40 ( 9 )   936 - 938   2011.9

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    DOI: 10.1246/cl.2011.936

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  • Indirect Cation-Flow Method: Flash Generation of Alkoxycarbenium Ions and Studies on the Stability of Glycosyl Cations

    Kodai Saito, Koji Ueoka, Kouichi Matsumoto, Seiji Suga, Toshiki Nokami, Jun-ichi Yoshida

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   50 ( 22 )   5153 - 5156   2011

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  • Organic reactions mediated by electrochemically generated ArS+

    Kouichi Matsumoto, Seiji Suga, Jun-ichi Yoshida

    ORGANIC & BIOMOLECULAR CHEMISTRY   9 ( 8 )   2586 - 2596   2011

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  • Cationic Three-component Coupling Involving an Optically Active Enamine Derivative. From Time Integration to Space Integration of Reactions

    Seiji Suga, Daisuke Yamada, Jun-ichi Yoshida

    CHEMISTRY LETTERS   39 ( 4 )   404 - 406   2010.4

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    DOI: 10.1246/cl.2010.404

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  • Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry

    Shunsuke Fujie, Kouichi Matsumoto, Seiji Suga, Toshiki Nokami, Jun-ichi Yoshida

    TETRAHEDRON   66 ( 15 )   2823 - 2829   2010.4

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  • 有機電解法による活性種蓄積と有機合成への応用

    菅 誠治

    電気化学および工業物理化学 : denki kagaku   78 ( 3 )   202 - 207   2010.3

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    DOI: 10.5796/electrochemistry.78.202

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  • Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids

    Koichi Mitsudo, Takuya Shiraga, Jun-ichi Mizukawa, Seiji Suga, Hideo Tanaka

    CHEMICAL COMMUNICATIONS   46 ( 48 )   9256 - 9258   2010

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    DOI: 10.1039/c0cc02633f

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  • Direct and indirect electrochemical generation of alkoxycarbenium ion pools from thioacetals

    Kouichi Matsumoto, Koji Ueoka, Shinkiti Suzuki, Seiji Suga, Jun ichi Yoshida

    Tetrahedron   65 ( 52 )   10901 - 10907   2009.12

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    DOI: 10.1016/j.tet.2009.09.020

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  • Thiofluorination of Carbon-Carbon Multiple Bonds Using Electrochemically Generated ArS(ArSSAr)+BF4-

    Shunsuke Fujie, Kouichi Matsumoto, Seiji Suga, Jun-ichi Yoshida

    CHEMISTRY LETTERS   38 ( 12 )   1186 - 1187   2009.12

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    DOI: 10.1246/cl.2009.1186

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  • Generation of diarylcarbenium ion poolsviaelectrochemical C-H bond dissociation

    Masayuki Okajima, Kazuya Soga, Takashi Watanabe, Kimitada Terao, Toshiki Nokami, Seiji Suga, Jun Ichi Yoshida

    Bulletin of the Chemical Society of Japan   82 ( 5 )   594 - 599   2009

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    DOI: 10.1246/bcsj.82.594

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  • Addition of ArSSAr to dienes via intramolecular C-C bond formation initiated by a catalytic amount of ArS+

    Kouichi Matsumoto, Shunsuke Fujie, Seiji Suga, Toshiki Nokami, Jun Ichi Yoshida

    Chemical Communications   ( 36 )   5448 - 5450   2009

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    DOI: 10.1039/b910821a

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  • Practical electrochemical iodination of aromatic compounds

    Kazuhide Kataoka, Yuji Hagiwara, Koji Midorikawa, Seiji Suga, Jun Ichi Yoshida

    Organic Process Research and Development   12 ( 6 )   1130 - 1136   2008.11

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  • Synthesis of thiochromans based on indirect cation pool method

    Kouichi Matsumoto, Koji Ueoka, Shunsuke Fujie, Seiji Suga, Jun ichi Yoshida

    Heterocycles   76 ( 2 )   1103 - 1119   2008.11

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    DOI: 10.3987/COM-08-S(N)64

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  • Electro-initiated coupling reactions of N-acyliminium ion pools with arylthiomethylsilanes and aryloxymethylsilanes

    Seiji Suga, Ikuo Shimizu, Yosuke Ashikari, Yusuke Mizuno, Tomokazu Maruyama, Jun ichi Yoshida

    Chemistry Letters   37 ( 9 )   1008 - 1009   2008.9

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    DOI: 10.1246/cl.2008.1008

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  • Microflow system controlled carbocationic polymerization of vinyl ethers

    Aiichiro Nagaki, Takeshi Iwasaki, Kohsuke Kawamura, Daisuke Yamada, Seiji Suga, Tuyoshi Ando, Mitsuo Sawamoto, Jun Ichi Yoshida

    Chemistry - An Asian Journal   3 ( 8-9 )   1558 - 1567   2008.9

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    DOI: 10.1002/asia.200800081

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  • Iterative molecular assembly based on the cation-pool method. Convergent synthesis of dendritic molecules

    Toshiki Nokami, Kousuke Ohata, Masafumi Inoue, Hiroaki Tsuyama, Akito Shibuya, Kazuya Soga, Masayuki Okajima, Seiji Suga, Jun Ichi Yoshida

    Journal of the American Chemical Society   130 ( 33 )   10864 - 10865   2008.8

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  • An electroinitiated cation chain reaction: Intramolecular carbon-carbon bond formation between thioacetal and olefin groups

    Kouichi Matsumoto, Shunsuke Fujie, Koji Ueoka, Seiji Suga, Jun Ichi Yoshida

    Angewandte Chemie - International Edition   47 ( 13 )   2506 - 2508   2008.3

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    DOI: 10.1002/anie.200705748

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  • Electrochemical generation of glycosyl triflate pools

    Toshiki Nokami, Akito Shibuya, Hiroaki Tsuyama, Seiji Suga, Albert A. Bowers, David Crich, Jun Ichi Yoshida

    Journal of the American Chemical Society   129 ( 35 )   10922 - 10928   2007.9

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  • Reactions of a N-acyliminium ion pool with benzylsilanes. Implication of a radical/cation/radical cation chain mechanism involving oxidative C-Si bond cleavage

    Tomokazu Maruyama, Yusuke Mizuno, Ikuo Shimizu, Seiji Suga, Jun Ichi Yoshida

    Journal of the American Chemical Society   129 ( 7 )   1902 - 1903   2007.2

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  • マイクロリアクターによる有機電解合成

    吉田 潤一, 菅 誠治

    電気化学および工業物理化学 : denki kagaku   75 ( 1 )   58 - 62   2007.1

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    DOI: 10.5796/electrochemistry.75.58

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  • Oxidative generation of diarylcarbenium ion pools

    Masayuki Okajima, Kazuya Soga, Toshiki Nokami, Seiji Suga, Jun Ichi Yoshida

    Organic Letters   8 ( 22 )   5005 - 5007   2006.10

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    DOI: 10.1021/ol061647c

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  • Organic synthesis using carbocations generated by electron transfer reactions

    Seiji Suga

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   64 ( 10 )   1010 - 1020   2006.10

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    DOI: 10.5059/yukigoseikyokaishi.64.1010

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  • Electroauxiliary-assisted sequential introduction of organic groups on the α-carbons of nitrogen

    Seiji Suga, Mitsuru Watanabe, Chun Hong Song, Jun Ichi Yoshida

    Electrochemistry   74 ( 8 )   672 - 679   2006.8

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    DOI: 10.5796/electrochemistry.74.672

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  • Distannane mediated reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving radical addition followed by electron transfer

    Tomokazu Maruyama, Seiji Suga, Jun ichi Yoshida

    Tetrahedron   62 ( 27 )   6519 - 6525   2006.7

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    DOI: 10.1016/j.tet.2006.03.114

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  • Indirect cation pool method. Rapid generation of alkoxycarbenium ion pools from thioacetals

    Seiji Suga, Kouichi Matsumoto, Koji Ueoka, Jun Ichi Yoshida

    Journal of the American Chemical Society   128 ( 24 )   7710 - 7711   2006.6

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    DOI: 10.1021/ja0625778

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  • Selective monoiodination of aromatic compounds with electrochemically generated I+ using micromixing

    Koji Midorikawa, Seiji Suga, Jun Ichi Yoshida

    Chemical Communications   ( 36 )   3794 - 3796   2006

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    DOI: 10.1039/b607284d

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  • Intramolecular participation in alkoxycarbenium ion pools

    Seiji Suga, Shinkiti Suzuki, Jun Ichi Yoshida

    Organic Letters   7 ( 21 )   4717 - 4720   2005.10

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  • Control of extremely fast competitive consecutive reactions using micromixing. Selective Friedel-Crafts aminoalkylation

    Aiichiro Nagaki, Manabu Togai, Seiji Suga, Nobuaki Aoki, Kazuhiro Mae, Jun Ichi Yoshida

    Journal of the American Chemical Society   127 ( 33 )   11666 - 11675   2005.8

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  • Electrochemical combinatorial organic syntheses using microflow systems

    Seiji Suga, Masayuki Okajima, Kazuyuki Fujiwara, Jun Ichi Yoshida

    QSAR and Combinatorial Science   24 ( 6 )   728 - 741   2005.8

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    DOI: 10.1002/qsar.200440003

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  • Cycloaddition of "N-Acyliminium ion pools" with carbon-carbon multiple bonds

    Seiji Suga, Yamato Tsutsui, Aiichiro Nagaki, Jun Ichi Yoshida

    Bulletin of the Chemical Society of Japan   78 ( 7 )   1206 - 1217   2005.7

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    DOI: 10.1246/bcsj.78.1206

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  • Radical addition to "cation pool". Reverse process of radical cation fragmentation

    Tomokazu Maruyama, Seiji Suga, Jun Ichi Yoshida

    Journal of the American Chemical Society   127 ( 20 )   7324 - 7325   2005.5

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    DOI: 10.1021/ja0511218

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  • "Cation pool" method based on C-C bond dissociation. Effective generation of monocations and dications

    Masayuki Okajima, Seiji Suga, Kenichiro Itami, Jun Ichi Yoshida

    Journal of the American Chemical Society   127 ( 19 )   6930 - 6931   2005.5

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    DOI: 10.1021/ja050414y

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  • Selective organic reactions using microreactors

    Jun Ichi Yoshida, Seiji Suga, Aiichiro Nagaki

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   63 ( 5 )   511 - 522   2005.5

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    DOI: 10.5059/yukigoseikyokaishi.63.511

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  • Microflow electroorganic synthesis without supporting electrolyte

    Roberto Horcajada, Masayuki Okajima, Seiji Suga, Jun Ichi Yoshida

    Chemical Communications   ( 10 )   1303 - 1305   2005.3

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  • Enhancement of chemical selectivity by microreactors

    Jun Ichi Yoshida, Aiichiro Nagaki, Takeshi Iwasaki, Seiji Suga

    Chemical Engineering and Technology   28 ( 3 )   259 - 266   2005.3

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    DOI: 10.1002/ceat.200407127

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  • Living cationic polymerization based on "cation pool" method using microsystem

    Aiichiro Nagaki, Jun Ichi Yoshida, Kohsuke Kawamura, Mitsuo Sawamoto, Seiji Suga, Tsuyoshi Ando

    2005 AIChE Spring National Meeting, Conference Proceedings   3021   2005

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  • Cation pool-initiated controlled/living polymerization using microsystems

    Aiichiro Nagaki, Kohsuke Kawamura, Seiji Suga, Tsuyoshi Ando, Mitsuo Sawamoto, Jun Ichi Yoshida

    Journal of the American Chemical Society   126 ( 45 )   14702 - 14703   2004.11

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    DOI: 10.1021/ja044879k

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  • Three-component coupling based on the "cation pool" method

    Seiji Suga, Tomoaki Nishida, Daisuke Yamada, Aiichiro Nagaki, Jun Ichi Yoshida

    Journal of the American Chemical Society   126 ( 44 )   14338 - 14339   2004.11

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    DOI: 10.1021/ja0455704

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  • Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

    Shinkiti Suzuki, Kouichi Matsumoto, Kohsuke Kawamura, Seiji Suga, Jun Ichi Yoshida

    Organic Letters   6 ( 21 )   3755 - 3758   2004.10

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  • Cationic carbohydroxylation of alkenes and alkynes using the cation pool method

    Seiji Suga, Yasuhisa Kageyama, Govindarajulu Babu, Kenichiro Itami, Jun Ichi Yoshida

    Organic Letters   6 ( 16 )   2709 - 2711   2004.8

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  • Generation of carbon free radicals by reduction of the cation pool

    Seiji Suga, Shinkiti Suzuki, Tomokazu Maruyama, Jun Ichi Yoshida

    Bulletin of the Chemical Society of Japan   77 ( 8 )   1545 - 1554   2004.8

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    DOI: 10.1246/bcsj.77.1545

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  • Highly selective friedel-crafts reaction of electrochmemically generated "cation pool" using micromixing

    Jun Ichi Yoshida, Aiichiro Nagaki, Seiji Suga

    Proceedings - Electrochemical Society   10   141 - 144   2004

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  • "N-acyliminium ion pool" as a heterodiene in [4 + 2] cycloaddition reaction

    Seiji Suga, Aiichiro Nagaki, Yamato Tsutsui, Jun Ichi Yoshida

    Organic Letters   5 ( 6 )   945 - 947   2003.3

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  • Highly selective Friedel-Crafts monoalkylation using micromixing

    Seiji Suga, Aiichiro Nagaki, Jun Ichi Yoshida

    Chemical Communications   3 ( 3 )   354 - 355   2003

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    DOI: 10.1039/b211433j

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  • Electroauxiliary-assisted sequential introduction of two carbon nucleophiles on the same α-carbon of nitrogen: Application to the synthesis of spiro compounds

    Seiji Suga, Mitsuru Watanabe, Jun ichi Yoshida

    Journal of the American Chemical Society   124 ( 50 )   14824 - 14825   2002.12

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    DOI: 10.1021/ja028663z

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  • Basic concepts of "cation pool" and "cation flow" methods and their applications in conventional and combinatorial organic synthesis

    Jun Ichi Yoshida, Seiji Suga

    Chemistry - A European Journal   8 ( 12 )   2650 - 2658   2002.6

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    DOI: 10.1002/1521-3765(20020617)8:12<2650::AID-CHEM2650>3.0.CO;2-S

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  • カチオンフロー法を用いたシリアルコンビナトリアル合成

    吉田 潤一, 菅 誠治

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN   60 ( 5 )   482 - 483   2002.5

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    DOI: 10.5059/yukigoseikyokaishi.60.482

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  • Reduction of a "cation pool": A new approach to radical mediated C-C bond formation

    S. Suga, S. Suzuki, J. I. Yoshida

    Journal of the American Chemical Society   124 ( 1 )   30 - 31   2002.1

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  • Catalytic enantioselective addition of dialkylzincs to aldehydes using (2S)-(-)-3-exo-(dimethylamino)isoborneol [(2S)-daib]: (S)-1-phenyl-1-propanol: [Benzenemethanol, α-ethyl-, (S)-]

    Masato Kitamura, Hiromasa Oka, Seiji Suga, Ryoji Noyori, David E. Kaelin, Stephen F. Martin, Gregory L. Beutner, Scott E. Denmark

    Organic Syntheses   79   139   2002

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    DOI: 10.15227/orgsyn.079.0139

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  • Selective electrochemical oxidation of heteroatom compounds having both silicon and tin on the same carbon as electroauxiliaries

    J. I. Yoshida, M. Watanabe, H. Toshioka, M. Imagawa, S. Suga

    Journal of Electroanalytical Chemistry   507 ( 1-2 )   55 - 65   2001.7

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    DOI: 10.1016/S0022-0728(01)00402-8

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  • Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives

    Seiji Suga, Masayuki Okajima, Jun ichi Yoshida

    Tetrahedron Letters   42 ( 11 )   2173 - 2176   2001.3

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    DOI: 10.1016/S0040-4039(01)00128-9

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  • Self and nonself recognition of chiral catalysts: The origin of nonlinear effects in the amino-alcohol catalyzed asymmetric addition of diorganozincs to aldehydes

    Ryoji Noyori, Seiji Suga, Hiromasa Oka, Masato Kitamura

    Chemical Records   1 ( 2 )   85 - 100   2001

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    DOI: 10.1002/tcr.1.abs

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  • Intramolecular assistance of electron transfer from heteroatom compounds. Electrochemical oxidation of 2-(2-pyridyl)ethyl-substituted ethers, sulfides, and selenides

    Mitsuru Watanabe, Seiji Suga, Jun Ichi Yoshida

    Bulletin of the Chemical Society of Japan   73 ( 1 )   243 - 247   2000.1

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    DOI: 10.1246/bcsj.73.243

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  • Direct oxidative carbon-carbon bond formation using the 'cation pool' Method. 1. Generation of iminium cation pools and their reaction with carbon nucleophiles

    Jun Ichi Yoshida, Seiji Suga, Shinkiti Suzuki, Naoya Kinomura, Atsushi Yamamoto, Kazuyuki Fujiwara

    Journal of the American Chemical Society   121 ( 41 )   9546 - 9549   1999.10

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    DOI: 10.1021/ja9920112

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  • Control of the free radical reaction by dynamic coordination: Unique reactivity of pyridylethyl-substituted tin hydrides

    Seiji Suga, Takao Manabe, Jun Ichi Yoshida

    Chemical Communications   ( 13 )   1237 - 1238   1999.7

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    DOI: 10.1039/a903795k

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  • 2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis

    Jun ichi Yoshida, Kenichiro Itami, Koichi Mitsudo, Seiji Suga

    Tetrahedron Letters   40 ( 17 )   3403 - 3406   1999.4

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  • General and efficient method for the synthesis of alkoxymethylsilanes

    Seiji Suga, Keiko Miyamoto, Mitsuru Watanabe, Jun Ichi Yoshida

    Applied Organometallic Chemistry   13 ( 6 )   469 - 474   1999

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    DOI: 10.1002/(SICI)1099-0739(199906)13:6<469::AID-AOC872>3.0.CO;2-A

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  • 2-(2-pyridyl)ethylsilyl group as a new class of electroauxiliary. Fine tuning of the electron transfer driven reactions by the dynamic coordination to silicon

    Jun Ichi Yoshida, Seiji Suga, Ken Ichi Fuke, Mitsuru Watanabe

    Chemistry Letters   ( 3 )   251 - 252   1999

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    DOI: 10.1246/cl.1999.251

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  • Quantitative analysis of the chiral amplification in the amino alcohol- promoted asymmetric alkylation of aldehydes with dialkylzincs

    Masato Kitamura, Seiji Suga, Hiromasa Oka, Ryoji Noyori

    Journal of the American Chemical Society   120 ( 38 )   9800 - 9809   1998.9

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    DOI: 10.1021/ja981740z

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  • Competition between electroauxiliaries. Selective electrochemical oxidation of heteroatom compounds having silicon and tin on the same carbon

    Jun Ichi Yoshida, Mitsuru Watanabe, Hideaki Toshioka, Masayuki Imagawa, Seiji Suga

    Chemistry Letters   ( 10 )   1011 - 1012   1998

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    DOI: 10.1246/cl.1998.1011

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  • Homochiral and heterochiral dimers of the methylzinc alkoxide formed from dimethylzinc and enantiomeric 3-exo-(dimethylamino)isoborneol - Origin of the distinct differences in solution-phase behavior and crystal structures

    M. Kitamura, M. Yamakawa, H. Oka, S. Suga, R. Noyori

    Angewandte Chemie - International Edition in English   35 ( 17 )   1173 - 1181   1996

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  • Homochiral and heterochiral dimers of the methylzinc alkoxide formed from dimethylzinc and enantiomeric 3-exo-(dimethylamino)isoborneol - Origin of the distinct differences in solution-phase behavior and crystal structures

    Masato Kitamura, Masashi Yamakawa, Hiromasa Oka, Seiji Suga, Ryoji Noyori

    Chemistry - A European Journal   2 ( 9 )   1173 - 1181   1996

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/chem.19960020921

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  • Self and Nonself Recognition of Asymmetric Catalysts. Nonlinear Effects in the Amino Alcohol-Promoted Enantioselective Addition of Dialkylzincs to Aldehydes

    Masato Kitamura, Seiji Suga, Makoto Niwa, Ryoji Noyori

    Journal of the American Chemical Society   117 ( 17 )   4832 - 4842   1995.5

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ja00122a013

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  • Enantiomer recognition of asymmetric catalysts. Thermodynamic properties of homochiral and heterochiral dimers of the methylzinc alkoxide formed from dimethylzinc and enantiomeric 3-exo-(dimethylamino)isoborneol

    Masato Kitamura, Seiji Suga, Makoto Niwa, Ryoji Noyori, Zong Xi Zhai, Hiroshi Suga

    Journal of Physical Chemistry   98 ( 48 )   12776 - 12781   1994

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/j100099a048

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  • Syntheses of dibenzo[c,e][1,2]diselenin and related novel chalcogenide heterocyclic compounds

    Shizuaki Murata, Toshiyasu Suzuki, Akira Yanagisawa, Seiji Suga

    Journal of Heterocyclic Chemistry   28 ( 2 )   433 - 438   1991

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/jhet.5570280243

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  • Enantioselective addition of diorganozincs to aldehydes catalyzed by β-amino alcohols

    R. Noyori, S. Suga, K. Kawai, S. Okada, M. Kitamura, N. Oguni, M. Hayashi, T. Kaneko, Y. Matsuda

    Journal of Organometallic Chemistry   382 ( 1-2 )   19 - 37   1990.2

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/0022-328X(90)85212-H

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  • Enantioselective Addition of Dialkylzincs to Aldehydes Promoted by Chiral Amino Alcohols. Mechanism and Nonlinear Effect

    M. Kitamura, S. Okada, S. Suga, R. Noyori

    Journal of the American Chemical Society   111 ( 11 )   4028 - 4036   1989.5

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ja00193a040

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  • Enantioselective alkylation of carbonyl compounds. From stoichiometric to catalytic asymmetric induction

    R. Noyori, S. Suga, K. Kawai, S. Okada, M. Kitamura

    Pure and Applied Chemistry   60 ( 11 )   1597 - 1606   1988.1

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1351/pac198860111597

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  • Catalytic Asymmetric Induction. Highly Enantioselective Addition of Dialkylzincs to Aldehydes

    M. Kitamura, S. Suga, K. Kawai, R. Noyori

    Journal of the American Chemical Society   108 ( 19 )   6071 - 6072   1986

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    Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ja00279a083

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MISC

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Awards

  • Dohgane Prize

    2023.12   GRAMS  

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  • 令和5年度有機電子移動化学学術賞

    2023.6   (公)電気化学会 有機電子移動化学研究会   電気化学的に発生させた活性種を用いる高効率合成プロセスの開発

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  • 長瀬研究振興賞

    2012  

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  • BCSJ賞

    2005   日本化学会  

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  • 有機電子移動化学奨励賞

    2004   有機電子移動化学研究会  

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  • 有機合成化学奨励賞

    2004   有機合成化学協会  

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  • 有機合成化学協会研究企画賞

    1999   有機合成化学協会  

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Research Projects

  • トリメチルシリルシアニドを用いた電子移動駆動型シアノ化反応の開発

    Grant number:22K05115  2022.04 - 2025.03

    日本学術振興会  科学研究費助成事業  基盤研究(C)

    菅 誠治

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    Grant amount:\4160000 ( Direct expense: \3200000 、 Indirect expense:\960000 )

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  • Digitalization-driven Transformative Organic Synthesis (Digi-TOS)

    Grant number:21H05207  2021.09 - 2026.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Transformative Research Areas (A)

    大嶋 孝志, 小池 隆司, 笹野 裕介, 高須 清誠, 安田 誠, 山口 潤一郎, 菅 誠治, 跡部 真人, 外輪 健一郎, 滝澤 忍, 椴山 儀恵, 矢島 知子, 宮尾 知幸, 小島 諒介, 武田 和宏, 松原 誠二郎, 矢田 陽

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    Grant amount:\298350000 ( Direct expense: \229500000 、 Indirect expense:\68850000 )

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  • 触媒的有機反応の自動最適化のための反応モジュール開発

    Grant number:21H05214  2021.09 - 2026.03

    日本学術振興会  科学研究費助成事業  学術変革領域研究(A)

    菅 誠治

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    Grant amount:\41080000 ( Direct expense: \31600000 、 Indirect expense:\9480000 )

    1.触媒型反応のための電解モジュールを使った反応の機械学習による反応最適化
    電解反応はエネルギー効率の悪い熱的エネルギーに頼らない本質的にエネルギーロスの少ない手法であるが、電極の電位の設定や電気量、さらにそれぞれの条件で溶媒や支持電解質などの電気化学的な反応パラメータが多く、これらを最適化に多くの時間と労力を費やす場合が多い。本年度は、これらの反応パラメータを連続的に変化させることのできる電解フローセルを用いて、多量のデータを効率よく取得し、機械学習を使って最短時間で反応の最適条件へと導く研究を行った。具体的な反応として、触媒量の電子で駆動するトリメチルシリルシアニドとカルボニル化合物の反応およびアセトニトリルやニトロメタンとカルボニル化合物の反応を取り上げ、A02班の滝澤らとの共同研究により、機械学習を用いて、最も収率のよい条件を短時間で見つけることが可能となった。また、同じフローシステムを用いて、時間当たりの生産量を最大限にする条件も機械学習を使って容易に見出すことことができることも示すことができた。
    2.条件探索を迅速に行うための最適な反応モジュールを開発
    一般に、フロー反応系でのデータ取得は人の手を介さないために再現性が高く、また、パラメータを変えて連続的にデータを取得することができるので、ネガティブデータを含めて大量かつ信頼性の高いデータを得るのに向いている。本年度はインライン分析をフロー系に組み込んだ、データのリアルタイムでの取得のためのシステム構築を行い、ReactIR(総括班の予算で購入)を中核としたフローシステムを作製した。今後は、触媒を担持した固体相を充填したカートリッジ型の反応モジュールを作製し、これを用いて条件の異なる反応を連続的に行い、高い質と豊富な量のデータを取得するシステムを完成させる予定である。

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  • Application of Chiral Nucleophilic Catalysts for Highly Difficult Molecular Transformations

    Grant number:19K05456  2019.04 - 2022.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    Mandai Hiroki

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    Grant amount:\4290000 ( Direct expense: \3300000 、 Indirect expense:\990000 )

    In order to further exploration of difficult molecular transformations reactions using binaphthyl-based DMAP derivatives, we worked on (1) structural elucidation of N-acylpyridinium salts important for enantioselectivity, (2) development of enantioselective (or regioselective) acylation of polyols, and (3) development of simple immobilized catalysts for acylation. In each research field, In each of these research items, we were able to obtain unprecedented knowledge. In particular, we obtained various the acylation of polyols yielded results that exceeded our initial expectations.

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  • Stereoselective nucleophilic additions to cyclic organocations: Inversion of stereochemistry and their utility for asymmetric synthesis

    Grant number:19K05478  2019.04 - 2022.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    Suga Seiji

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    Grant amount:\4420000 ( Direct expense: \3400000 、 Indirect expense:\1020000 )

    Various cyclic N-acyliminium ions having substituents derived from piperidine (6-membered ring) and pyrrolidine (5-membered ring) were generated by the indirect cation pool method, and the stereoselectivity in the reaction with various nucleophiles was examined. As a result, we found a phenomenon that the stereoselectivity was completely inversed by changing the nucleophiles, and clarified that the structure of the nucleophile and the counterion of the organic cation strongly affected the phenomenon. Asymmetric synthesis of disubstituted cyclic alkaloids using this phenomenon was also performed, and four stereoisomers with an enantiomeric excess of almost 100% from a single cation precursor were successfully obtained.

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  • 反応集積化に適した高活性反応プロモーターを用いるマイクロフローシステムの開発

    Grant number:18H04415  2018.04 - 2020.03

    日本学術振興会  科学研究費助成事業  新学術領域研究(研究領域提案型)

    菅 誠治

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    Grant amount:\4680000 ( Direct expense: \3600000 、 Indirect expense:\1080000 )

    反応集積化のためのキーテクノロジーとして注目されているマイクロフロー合成システムに着目し、これらを用いて有機電子移動反応により発生させた高活性な均一系触媒やプロモーターを用いた高速で効率的な触媒型反応を実現すること、およびこれを集積化することを目的として研究を行った。令和元年度はとくに下記の課題について重点的に取り組んだ。
    1.アセトニトリル溶媒中での電解反応のよるシアノメチル化反応
    アセトニトリルにアルデヒド溶解させた溶液に触媒量の電気を通電し還元反応を行うと、対応するシアノメチル化体が得られることが報告されている。この反応は操作的に単純で非常にクリーン、かつ、原子効率の高い反応であるが、再現性に乏しく、また、反応機構も不明であった。本年度は当研究室で独自に開発したマイクロフロー電解リアクターを用いて、各種ベンズアルデヒド誘導体、さらには脂肪族アルデヒドやα,β-不飽和アルデヒドなどを基質として反応条件を精査した。その結果、マイクロフロー系での反応がバッチ系と比較して格段に反応効率が向上することがわかった。再現性も確保できた。
    2.電解還元により開始されるシアノシリル化反応
    上記マイクロフロー電解リアクターを用いた反応探索の中で、アルデヒドとトリメチルシリルシアニドを共存させた状態で電解還元を行うと、ごく少量の電気量を通電するだけで、アルデヒドのシアノシリル化が高効率で進行することを見出した。本年度はマイクロフロー系でこの反応の汎用性を調査したところ、多様なアルデヒドのみならず、ケトンにおいても高い収率で進行することを明らかにした。

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  • Nucleophilic Additions to Cyclic N-Acyliminium Ions: Inverse Stereoselectivity

    Grant number:16K05777  2016.04 - 2019.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    Suga Seiji

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    Grant amount:\4940000 ( Direct expense: \3800000 、 Indirect expense:\1140000 )

    Cyclic alkaloids often have high biological activity, and development of their stereoselective synthesis is one of the most important issues in this research area. In this study, the stereochemistry in the reaction of the N-acyliminium ion intermediates generated by the indirect cation pool method was investigated. As a result of research focusing on the inverse stereochemistry phenomena, we show the generality of this phenomenon. In addition, some control experiments were conducted for the elucidation of mechanism of this phenomenon, and applications were also examined.

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  • マイクロフローシステムによる高活性反応プロモーターの発生と合成反応の集積化

    Grant number:16H01155  2016.04 - 2018.03

    日本学術振興会  科学研究費助成事業  新学術領域研究(研究領域提案型)

    菅 誠治

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    Grant amount:\5720000 ( Direct expense: \4400000 、 Indirect expense:\1320000 )

    我々は電気的化学的酸化・還元に対する可逆性を有し、温度耐性にも優れた有機ジカチオン種を生成させる方法を見出してきた。バッチ反応系おいてこの有機ジカチオンは高い触媒活性をもち、また、レドックス応答型の触媒としても用いることができる。本新領域研究では、この有機ジカチオン種化学をマイクロフロー系へと展開させることにより、触媒反応の開始と停止を触媒量の電気化学的なレドックスフロー系で実現できれば、後続反応に影響を与えることのない効率的な集積型反応フローシステムを構築できるのではないかと考え研究を推進した。
    本年度は、前年度までに新規に設計・外注した電解用マイクロリアクターを用いて向山アルドール反応を行った。中性分子である有機ジカチオン前駆体とアルデヒド、エノールシリルエーテルの混合溶液を少量の電気量で陽極酸化することにより、フロー系内で有機ジカチオン種を発生させることにより(触媒の活性化)反応をスタートさせ、短いチューブ内で反応完結後、この溶液を陰極側へと導くことにより有機ジカチオン種を還元し中性分子に戻す(触媒の不活性化)ことで反応を停止させた。反応は非常に効率よく進行した。現在このフロー系を用いた後続反応について検討を行っている。
    また、別の反応として、少量の電気量で開始されるシアノメチル化反応を取り上げ、研究を行った。アセトニトリル中、様々な芳香族アルデヒド誘導体を触媒量の電気量で電解還元することで、対応するシアノメチル化体が得られるという非常にシンプルな反応系を見出した。これも反応集積化に適した反応と言える。現時点では一部脱水反応もあわせておこり、収率も中程度であるが、反応剤を使う必要がないため、容易に後続反応へつなげることができるという意味で、非常に興味深い反応系である。現在、フロー系への展開を行っている。

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  • Deepening and Developing New Aspects of Flash Chemistry

    Grant number:26220804  2014.05 - 2019.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (S)

    YOSHIDA Jun-ichi, Nagaki Aiichiro, Simizu Akihiro, Tonomura Osamu, Suga Seiji, Kim Heejin

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    Grant amount:\192010000 ( Direct expense: \147700000 、 Indirect expense:\44310000 )

    In this project, we deepened the concept of flash chemistry, which is a chemical synthesis using extremely fast reactions (seconds to milliseconds order) based on flow chemistry and developed new applications in organic synthesis by rational design of reactions based on the quantitative analysis using temperature-residencetime mapping and kinetic studies.

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  • 電気化学反応が駆動する有機分子触媒反応の開発

    Grant number:26105740  2014.04 - 2016.03

    日本学術振興会  科学研究費助成事業  新学術領域研究(研究領域提案型)

    菅 誠治

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    Grant amount:\6760000 ( Direct expense: \5200000 、 Indirect expense:\1560000 )

    本研究はレドックスにより触媒の機能(活性)をコントロールすることにより、化学反応の反応速度を「触媒の量」により制御する新しい反応プロセスの制御法の提出を主眼とするものである。とくに、有機カチオン前駆体と有機カチオンを電気化学的な酸化・還元により相互変換することにより、レドックスに応答して触媒反応のスイッチ オン・オフが可能な有機分子触媒反応系の実現をめざして研究を推進した。
    昨年度までに、レドックス可逆性をもつ有機カチオン前駆体と有機ジカチオンの相互変換を行うことにより、向山アルドール反応において反応のスイッチオンとオフを繰り返し行うことができることが可能となった。H27年度はこのレドックス応答性の触媒系が、他の反応に応用できるかどうかを中心に検討を行った。その結果、Nazarov環化反応やシアノシリル化反応においても、反応のスイッチオンとオフを繰り返し行うことができることが明らかになった。この反応制御法は従来の温度や濃度といった反応速度制御因子ではなく、「触媒の量」により反応速度をコントロールできるという全く新しい方法論を提供できた点において極めて意義深い。とくに、有機物のみからなる触媒を用いてレドックス応答性分子触媒系を実現した系は初めてである。
    さらに、多様な有機カチオンの構造と触媒活性の相関についても引き続き検討を行い、カチオン中心の電子状態と基質の触媒へのアクセシビリティ―の両方が触媒活性に極めて大きな影響を与えることがわかった。
    アミン系の有機触媒と電気化学を組み合わせた新しい触媒反応系の構築についても検討したが、きれいな反応系を構築するには至らず、その点に課題が残った。

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  • Stereoselective Synthesis of Cyclic Alkaloids Using the Cation Pool Method

    Grant number:25410117  2013.04 - 2016.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    SUGA SEIJI

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    Grant amount:\5200000 ( Direct expense: \4000000 、 Indirect expense:\1200000 )

    The purpose of the present research is to reveal the mechanistic insight of diastereoselective synthesis of di-substituted piperidine derivatives accomplished by the reaction of N-acyliminium ions, which are prepared by the Indirect Cation Pool Method. The reactions of highly reactive N-acyliminium ions having a piperidine skeleton with a substituent, generated and accumulated from the corresponding thioaminals by the treatment of electrochemically generated arylsulfonium ion pool, with carbon nucleophiles gave rise to the formation of the corresponding of di-substituted piperidine derivatives in a highly-stereoselective manner. We validated the relationship of the conformations of cationic intermediates and stereoselectivities. The conformations of the N-acyliminium ions were determined by NMR spectroscopy, and the origin of the stereoselectivity was mostly clarified.

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  • レドックス応答型有機分子触媒の活性制御を利用した反応スイッチング

    Grant number:24105522  2012.04 - 2014.03

    日本学術振興会  科学研究費助成事業  新学術領域研究(研究領域提案型)

    菅 誠治

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    Grant amount:\9490000 ( Direct expense: \7300000 、 Indirect expense:\2190000 )

    レドックス(酸化・還元)に応答して機能や物性が変化する有機化合物が材料科学の観点から注目を集めている。最近では、レドックスにより触媒の機能(活性)をコントロールしようとする試みも行われるようになってきた。この方法が実現できれば、化学反応の反応速度を化学的にコントロールでき、反応プロセスの新しい制御法になりうるのではないかと期待される。
    一方、我々は、これまでに電気化学的な酸化・還元反応により創製した高活性な化学種を用いた新規有機反応の開発に取り組んできた。たとえば、ある種の化合物を低温で電気化学的に酸化すると炭素-炭素結合が選択的に切断され、対応する有機ジカチオン(カチオンプール)を蓄えることに成功している。
    このような背景のもと、昨年に引き続いて、有機カチオン前駆体と有機カチオンを電気化学的な酸化・還元により相互変換することにより、レドックスに応答して触媒反応のスイッチ オン・オフが可能な有機分子触媒反応系の実現をめざして研究を推進した。その結果、向山アルドール反応やNazarov環化反応で、共存させた有機カチオン前駆体を選択的に電気化学的に酸化することで有機ジカチオン種を発生させることにより、触媒反応を開始させ、また、この反応系に対してやはり電気化学的な還元を行うことで、反応を停止させることに成功した。さらに、これを繰り返すことで、触媒反応のスイッチ オン・オフを繰り返すことも可能となった。
    また、有機カチオン前駆体と有機カチオン間のレドックスによる可逆性向上のための新規な有機カチオン前駆体の合成やエナンチオ選択的な反応へ展開するためにキラルな有機カチオン前駆体の合成にも取り組み、それぞれの有機カチオン前駆体の合成にも成功した。

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  • Electrochemically generated trifluoromethyl cation equivalent

    Grant number:23655085  2011 - 2012

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Exploratory Research

    SUGA Seiji

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    Grant amount:\3900000 ( Direct expense: \3000000 、 Indirect expense:\900000 )

    Generation of trifluoromethyl cation equivalents via electrochemical oxidation of trifluoroacetic acid was examined. Although we have not get trifluoromethyl cation equivalents in hand、some important information concerning oxidation of trifluoroacetic acid was obtained. Oxidation potential of trifluoroacetic acid was decreased by ether additives. Electrochemical microflow reactors are potential tools to effectively oxidize trifluoroacetic acid for the trifluoromethylation.

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  • Multi-component coupling reactions based on the additions of cation pools to carbon-carbon multiple bonds

    Grant number:18350020  2006 - 2008

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    SUGA Seiji

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    Grant amount:\16060000 ( Direct expense: \14800000 、 Indirect expense:\1260000 )

    Multi-component coupling reactions, especially three-component reactions based on the sequential additions of nucleophiles and electrophiles to carbon-carbon multiple bonds are quite important to provide a variety of organic compounds ; however, there are few examples of the reactions initiated by the additions of carbocations to carbon-carbon multiple bonds. In this project, we focus on the development of this type of cationic multi-component couplings on the basis of the cattion pool method. We have developed a new method to construct a substituted tetrahydrofuran ring in a highly stereoselective manner by using intramolecular cationic carbo-hydroxylation, and a method to provide chiral diamino alcohols which is based on the sequential C-C bond formations initiated by the addition of a cation pool to an enamide.

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  • Generations and Reactions of Reactive Organic Cations Using Flow Redox Systems

    Grant number:15350056  2003 - 2005

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    SUGA Seiji

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    Grant amount:\15300000 ( Direct expense: \15300000 )

    Recently we have developed the "cation pool" method, which involves generation of highly reactive carbocations by low temperature electrolysis followed by reactions with a variety of nucleophiles. Micro flow reactors have received significant interest in the stream of downsizing of chemistry, and they are expected to make an innovative and revolutionary change for chemical synthesis. The advantages of microflow reactors of easy modulation and the possibility of combining reactors are quite useful to construct flow type redox systems for the organic transformations. On the basis of this concept we have developed "cation flow" method using microflow electrochemical reactors, which involves generation of highly reactive carbocations by low temperature electrolysis. This method enables the manipulation of carbocation intermediates to achieve direct oxidative C-C bond formation. Based on the "cation flow" method, continuous sequential combinatorial synthesis can be accomplished by simple flow switching. As an extension of the "cation flow" method, an electrochemical paired micro flow system that involves concurrent anodic generation of carbocations and cathodic generation of carbon nucleophiles followed by their reactions to achieve straightforward C-C bond formation has been developed. Anodic methoxylation of several organic compounds have also been achieved in the absence of intentionally added supporting electrolyte using an electrochemical microflow system.

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  • 電解酸化を機軸とするヘテロ環化合物の新規合成法

    Grant number:13029049  2001 - 2003

    日本学術振興会  科学研究費助成事業  特定領域研究

    菅 誠治

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    Grant amount:\12600000 ( Direct expense: \12600000 )

    ヘテロ原子を含む化合物を反応基質とした電解酸化反応は、反応性に富むカチオンやラジカル活性種を発生させる手段として極めて有効であり、多岐にわたる合成反応への応用が期待されている。本研究では、{窒素や酸素などのヘテロ環化合物を低温で電解酸化することで、高反応活性炭素カチオンを発生させ、これらを用いた新規な分子変換法に焦点をあて研究を推進した。前年度までに低温電解酸化による炭素カチオンの創生と蓄積法「カチオンプール法」を用いて反応性に富む炭素カチオンである「N-アシルイミニウムイオン」および「オキシカルベニウムイオン」を蓄える(プールする)ことに成功し、各種炭素求核剤の直接カップリング反応に成功している。平成15年度は、蓄えたN-アシルイミニウムイオンのプールを1電子還元することで、ホモカカップリング生成物が得られること、ならびに、電子不足のアルケンとカップリング反応が進行することを見出した。また、N-アシルイミニウムイオンとアルケンあるいはアルキンなどの不飽和結合種が、[4+2]付加環化を起こすことも見出した。これらの手法は、ヘテロ環化合物の合成法として高い一般性を有し、新規な合成手法として意義深いものであると考えられる。

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  • Control of Electron Transfer Reactions on the Basis of Dynamic Intramolecular Coordination

    Grant number:13640532  2001 - 2002

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    SUGA Seiji

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    Grant amount:\3400000 ( Direct expense: \3400000 )

    The present work stems from our earlier observations that the introduction of carbonyl, alkoxy, and pyridyl groups decreases the oxidation potential of tetraalkylstannanes. There is no indication of the coordination in the neutral molecule by the spectroscopy. Therefore, the decrease of the oxidation potential seems to be attributed to the dynamic intramolecular coordination to tin in the cation radical intermediates. Such coordination stabilizes the cation radical which in turn favors the electron transfer and also controls the selectivity of the bond cleavage. Pyridyl group has been found to be especially effective among the examined.
    Thus new class of electroauxiliary, [2-(2-pyridyl)etyl]dimethylsilyl group has been developed. Introduction of 2-(2-pyridyl)ethyl group on silicon atom of α-silylethers and sulfides gives rise to decrease of their oxidation potentials. Studies based on NMR spectra, ab initio molecular orbital calculations, and solvent effect of oxidation have suggested that the decrease of the oxidation potentials is attributed to the 'dynamic intramolecular coordination' of pyridyl group to silicon. The reactivity of this new electroauxiliary has been compared with those of trimethylsilyl group and tributylstannyl group by competition experiments. The present study indicates the feasibility of fine tuning of the reactivity of electroauxiliaries using dynamic intramolecular coordination.

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  • Development of Practical Electron Transfer Driven Reactions for Organic Synthesis

    Grant number:11555242  1999 - 2001

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    YOSHIDA Jun-ichi, SUGA Seiji

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    Grant amount:\13500000 ( Direct expense: \13500000 )

    We aimed to develop a practical electron transfer driven reaction for organic synthesis, and a "cation flow"method has been developed on the basis of the "cation pool" method. In the "cation flow" method, carbocations generated using a low temperature electrochemical microflow reactor were immediately trapped with carbon nucleophies. Downsizing of a electrochemical flow reactor enables efficient temperature control and shortening ofa residence time, and thus an application of this system to less stable carbocation could be possible. We have also developed a direct analysis system of the flow of the carbocations using FITR spectrometer. More outstanding feature of the "cation flow" system is that continuous sequential combinatorial synthesis can be accomplished by simple flow switching. Although parallel syntheses enjoy versatile applications in combinatorial chemistry, the present continuous sequential method opens a new intriguing aspect of combinatorial synthesis.

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  • 自動合成を指向した光学活性ポリオール類の新規合成法

    Grant number:09750933  1997 - 1998

    日本学術振興会  科学研究費助成事業  奨励研究(A)

    管 誠治

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    Grant amount:\2200000 ( Direct expense: \2200000 )

    「合成ロボットを用いる自動合成」を指向した新規な光学活性ポリオール類の合成法の確立をめざし研究を行った。具体的には、(1)アルデヒド類に対するホルミルアニオン等価体の高立体選択的な付加反応を新しく開発し、(2)これを合成ロボットで連続的に繰り返すことで、光学活性ポリオール類の合成へと発展させる、とう2つの方法論を基盤とする。
    本年度は、前年度までに確立した酸素官能基を有するアルコキシメチルシランの他に、窒素官能基を有するアルコキシメチルシランを新規なホルミルアニオン等価体の前駆体として新たに設計・合成した。中でも、ケイ素上にジメチルアミノフエニル基を有するアルコキシメチルシランをヘキサン中、s-ブチルリチウムを塩基として用いて脱プロトン化後、アルデヒド化合物への付加反応を試みたところ、この反応がテトラメチルジアミンにより著しく加速され、対応するl-メトキシ-2-ヒドロキシシランを収率よく与えることがわかった。ヒドロキシル基をベンジル化した後、メタノール中で隔膜付きセルを用いて電解酸化すると、ケイ素がメトキシ基へと変換され、対応するアセタールが得られた。以上のことから、ジメチルアミノフエニル基を有するアルコキシメチルシランがホルミルアニオン等価体とし有効に作用することが明らかとなった。
    今後、キラルな配位子を系統的に検索することで発生させたアニオン種を「キラルなホルミルアニオン等価体」として用い、α-ヒドロキシアルデヒドに対するエナンチオ選択的な付加反応への展開が期待されるとともに、合成ロボットを用いたプロセスの自動化と組み合わせることで、光学活性ポリオール類の一般的合成法確立への足がかりになるものと考える。

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