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Chiral Amplification through Organocatalytic Photochirogenesis with Higher-Order Supramolecular Complex

Research Project

Project/Area Number 26620030
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

INOUE Yoshihisa  大阪大学, 工学(系)研究科(研究院), 教授 (30112543)

Co-Investigator(Kenkyū-buntansha) 森 直  大阪大学, 大学院工学研究科 (70311769)
福原 学  大阪大学, 大学院工学研究科 (30505996)
西嶋 政樹  大阪大学, 産学連携本部 (70448017)
Project Period (FY) 2014-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2014: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywords光化学 / 超分子化学 / 触媒的不斉合成 / 不斉増殖 / 高次錯体 / 水素結合 / 不斉合成
Outline of Final Research Achievements

Photochirogenesis has rapidly developed in recent years as an alternative methodology to complement the conventional asymmetric syntheses using chiral catalysts and enzymes. In the present study, we have achieved the simultaneous enhancement of reactivity and stereoselectivity in an enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid through the formation of a novel higher-order (2:2) complexation with L-prolinol, which was shown to be expandable to a wider range of photosubstrates with carboxylic acid moiety/ies. This enabled us to accomplish the organocatalytic supramolecular photochirogenesis for the first time, which is inherently difficult and hence has never been achieved in asymmetric synthesis mediated by a chiral template.

Report

(2 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • Research Products

    (3 results)

All 2015 2014

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 3 results,  Open Access: 1 results)

  • [Journal Article] Catalytic Supramolecular Photochirogenesis2015

    • Author(s)
      Z. Yan, W. Wu, C. Yang and Y. Inoue
    • Journal Title

      Supramolecular Catalysis

      Volume: 2

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Ammonia-Driven Chirality Inversion and Enhancement in Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate Mediated by Diguanidino-γ-cyclodextrin.2014

    • Author(s)
      Yao, J.; Yan, Z.; Ji, J.; Wu, W.; Yang, C.; Nishijima, M.; Fukuhara, G.; Mori, T.; Inoue, Y.
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 19 Pages: 6916-6919

    • DOI

      10.1021/ja5032908

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Mammalian serum albumins as a chiral mediator library for bio-supramolecular photochirogenesis: optimizing enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate.2014

    • Author(s)
      Nishijima, M.; Goto, M.; Fujikawa, M.; Yang, C.; Mori, T.; Wada, T.; Inoue, Y.
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 91 Pages: 14082-14085

    • DOI

      10.1039/c4cc04818k

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant

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Published: 2014-04-04   Modified: 2016-06-03  

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