文部科学省科学研究費助成事業「新学術領域研究（研究領域提案型）」平成29～33年度ハイブリッド触媒

林 雄二郎

所属 東北大学・理学系
役職 教授
連絡先 Email
HP http://www.ykbsc.chem.tohoku.ac.jp/
専門分野 有機合成化学
研究キーワード 有機触媒、全合成
所属学会・研究会 日本化学会、アメリカ化学会、有機合成化学協会

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概要

ドミノ反応は同一容器内で複数の反応を順次行うために、中間体を単離する必要がなく、反応間における精製工程を省略するので、操作時間の短縮、廃溶媒の低減といった利点を有する、環境調和型の反応である。申請者はこれまで、多くのドミノ反応を開発し、ドミノ反応を用いたプロスタグランジンA1およびE1メチルエステルのthree-pot合成、インフルエンザ治療薬タミフルのone-pot合成を達成した。有機触媒はドミノ反応に適した触媒である事に注目し、本研究では有機触媒を用いた不斉触媒反応を基盤とする、有用なドミノ反応を開発し、重要な光学活性合成中間体を、環調和型手法で効率的に合成する事を目的とする。また開発した手法を、強力な生物活性を有する天然物の全合成に応用し、その有用性を示す。具体的には多置換シクロペンタノン、ピロリジン、ピペリジンなどの炭素骨格、含窒素複素環骨格の新規ドミノ反応による不斉合成法を確立し、これらの骨格を有する天然有機化合物の短工程合成を検討する。

研究業績

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原著論文

  • "Asymmetric Synthesis of Pentasubstituted Cyclohexanes through Diphenylprolinol Silyl Ether Mediated Domino Michael/Michael Reaction"
    A. S. Odoh, L. Aidanpää, N. Umekubo, H. Matoba, N. Mori, Y. Hayashi
    Eur. J. Org. Chem., 2021, 6670-6673
  • "Synthesis of bicyclo[2.2.2]octanes with a quaternary bridgehead carbon by diphenylprolinol silyl ether mediated domino reaction"
    N. Umekubo, T. Taniguchi, K. Monde, Y. Hayashi
    Asian. J. Org. Chem., 2021, 10, 3261-3265
  • "Enantiodivergent one-pot synthesis of axially chiral biaryls using organocatalyst-mediated enantioselective domino reaction and central-to-axial chirality conversion"
    S. Koshino, T. Taniguchi, K. Monde, E. Kwon, Y. Hayashi
    Chem. Eur. J. , 2021, 27, 15786-15794
  • "Halogen Bonding of N-Halosuccinimides with Amines and Effects of Brønsted Acids in Quinuclidine-Catalyzed Halocyclizations"
    J. Li, E. Kwon, M. J. Lear, Y. Hayashi
    Helv. Chim. Acta, 2021, 104, e210080
  • "Asymmetric synthesis of functionalized 9-methyldecalins using a diphenylprolinol silyl ether-mediated domino Michael/Aldol reaction"
    Y. Hayashi, H. A. Salazar, S. Koshino
    Org. Lett., 2021, 23, 6654-6658
  • "Direct Cyclopropanation of -Cyano -Aryl Alkanes by Light Mediated Single Electron Transfer between Donor-Acceptor Pairs"
    J. Li, M. J. Lear, Y. Hayashi
    Chem. Eur. J. , 2021, 27, 5901-5905
  • "Oxidative Peptide Bond Formation of Glycine-Amino Acid using 2-(Aminomethyl)malononitrile as a Glycine Unit"
    X. Wang, J. Li, Y. Hayashi
    Chem. Commun. , 2021, 57, 4283-4286
  • "Time and Pot Economy in Total Synthesis"
    Y. Hayashi
    Acc. Chem. Res., 2021, 54, 1385-1398
  • "Time Economy in Total Synthesis"
    Y. Hayashi
    J. Org. Chem. , 2021, 86, 1-23
  • "Evidence for an enolate mechanism in the asymmetric Michael reaction of -unsaturated aldehydes and ketones via a hybrid system of two secondary amine catalysts"
    N. Umekubo, T. Terunuma, E. Kwon, Y. Hayashi
    Chem. Sci. , 11, 11293-11297
  • "Asymmetric Synthesis of Corey Lactone and Latanoprost"
    N. Umekubo, Y. Hayashi
    Eur. J. Org. Chem., 6221-6227
  • "Highly Enantioselective Access to syn-α, γ-Dihydroxycarbonyl Building Blocks via Organocatalyst-Mediated Aldol Reaction as a Key Step"
    Y. Hayashi, X. Wang, G. Kawauchi
    Chem. Lett., 49, 940-943
  • "One-pot synthesis of chiral cis-hydrindanes via diphenylprolinol silyl ether mediated domino reaction and aldol condensation"
    N. Umekubo, R. Iwata, *Y. Hayashi
    Chem. Lett., 49, 867-869
  • "Asymmetric Michael reaction of aldehydes and α-cyano α, β-unsaturated esters catalyzed by diphenylprolinol silyl ether; a facile asymmetric route to 3,4,5-trisubstituted piperidines"
    Y. Hayashi, A. S. Odoh, N. Kranidiotis-Hisatomi
    ChemCatChem., 12, 2412-2415
  • "Inversion of the Axial Information during Oxidative Aromatization in the Synthesis of Axially Chiral Biaryls with Organocatalysis as a Key Step"
    S. Koshino, A. Takikawa, K. Ishida, T. Taniguchi, K. Monde, E. Kwon, S. Umemiya, Y. Hayashi
    Chem. Eur. J., 26, 4525-4530
  • "Pot and time economies in the total synthesis of Corey lactone"
    N. Umekubo, Y. Suga, *Y. Hayashi
    Chem. Sci., 11, 1205-1209
  • "Pot-Economical Total Synthesis of Clinprost"
    Umekubo, N.; *Hayashi, Y.
    Org. Lett., 22, 9365-9370
  • "Asymmetric Domino Reaction of-Unsaturated Aldehydes and -Acyl -Unsaturated Cyclic Ketones Catalyzed by Diphenylprolinol Silyl Ether"
    *Hayashi, Y.; Suga, Y.; Umekubo, N.
    Org. Lett., 22, 8603-8607
  • "Evidence for an enolate mechanism in the asymmetric Michael reaction of -unsaturated aldehydes and ketones via a hybrid system of two secondary amine catalysts"
    Umekubo, N.; Terunuma, T.; Kwon, E.; *Hayashi, Y.
    Chem. Sci. , 11, 11293-11297
  • "214. Asymmetric Synthesis of Corey Lactone and Latanoprost"
    Umekubo, N.; *Hayashi, Y.
    Eur. J. Org. Chem., 6221-6227
  • "Asymmetric One-Pot Mukaiyama Michael/Michael reaction catalyzed by diphenylprolinol silyl ether"
    Umekubo, N.; Hayashi, Y.
    Eur. J. Org. Chem., 5596-5600
  • "Highly Enantioselective Access to syn-α, γ-Dihydroxycarbonyl Building Blocks via Organocatalyst-Mediated Aldol Reaction as a Key Step"
    *Hayashi, Y.; Wang, X.; Kawauchi, G.
    Chem. Lett., 49, 940-943
  • "One-pot synthesis of chiral cis-hydrindanes via diphenylprolinol silyl ether mediated domino reaction and aldol condensation"
    Umekubo, N.; Iwata, R.; Hayashi, Y.
    Chem. Lett., 49, 867-869
  • "Asymmetric Michael reaction of aldehydes and α-cyano α, β-unsaturated esters catalyzed by diphenylprolinol silyl ether; a facile asymmetric route to 3,4,5-trisubstituted piperidines"
    *Hayashi, Y.; Odoh, A. S.; Kranidiotis-Hisatomi, N.
    ChemCatChem, 12, 2412-2415
  • "Inversion of the Axial Information during Oxidative Aromatization in the Synthesis of Axially Chiral Biaryls with Organocatalysis as a Key Step"
    Koshino, S.; Takikawa, A.; Ishida, K.; Taniguchi, T.; Monde, K.; Kwon, E.; Umemiya, S.; *Hayashi, Y.
    Chem. Eur. J., 26, 4525-4530
  • "Pot and time economies in the total synthesis of Corey lactone"
    Umekubo, N.; Suga, Y., *Hayashi, Y.
    Chem. Sci., 11, 1205-1209
  • "Pot and time economies in the total synthesis of Corey lactone,"
    Umekubo, N.;Suga, Y.; Hayashi, Y.
    Chem. Sci., 2019年12月23日, 11, 1205-1209
  • "Asymmetric Synthesis of Biaryl Atropisomers Using an Organocatalyst-Mediated Domino Reaction as the Key Step"
    Hayashi, Y.;Takikawa, A.;Koshino, S.;Ishida, K.
    Chem. Eur. J., 2019年6月19日, 21, 10319-10322
  • "Asymmetirc Michael Reaction of -CF3 Thioester and -Unsaturated Aldehyde Catalyzed by Diphenylprolinol Silyl Ether"
    Hayashi, Y.;Yamda, T.; Sato, M.;Watanabe, S.;Kwon, E.;Iwasaki, K.;Umemiya, S.
    Org. Lett. , 2019年6月18日, 21, 5183-5186
  • "Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl ether"
    *Hayashi, Y; Toda, S.
    Synlett, 2019年1月, 30, 442-448
  • "Asymmetrci Michael Reaction of Aldehydes and Dicyanoalkenes Catalyzed by Diphenylprolinol Silyl Ether"
    *Hayashi, Y.; Kranidiotis-Hisatomi, N.; Sakamoto, D.; Oritani, K.; Kawamoto, T.; Kamimura, A.
    Eur. J. Org. Chem., 2018年11月6日, 6843-6847
  • "Domino Michael/Michael Reaction for the Formation of Chiral Spirocycles Using a Diphenylprolinol Silyl Ether"
    *Hayshi, Y.; Nagai, K.; Umemiya, S.
    Eur. J. Org. Chem., 2018年9月20日, 678-681
  • "Asymmetric Michael reaction of aldehyde and -substituted -nitroacrylate catalyzed by diphenylprolinol silyl ether"
    Sakamoto, D.; *Hayashi, Y.
    Chem. Lett., 2018年7月, 47(7), 833-835

総説・解説

  • 「有機触媒を用いたビアリール型軸不斉化合物の新規合成法の開発」 林　雄二郎, 化学工業, 38-47, 9, 2019年9月1日

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