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Challenge to Asymmetric Multicomponent Reactions Utilizing Chiral Amplification Phenomena in Helical Structures with a Minute Chiral Source

Research Project

Project/Area Number 17K19154
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Research Field Polymer, Organic materials, and related fields
Research InstitutionKanazawa University

Principal Investigator

Maeda Katsuhiro  金沢大学, ナノ生命科学研究所, 教授 (90303669)

Co-Investigator(Kenkyū-buntansha) 覚知 亮平  群馬大学, 大学院理工学府, 助教 (00743816)
Project Period (FY) 2017-06-30 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2018: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2017: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Keywords多成分連結反応 / 不斉増幅 / らせん / ポリアセチレン / 不斉反応 / 高分子合成 / らせん高分子
Outline of Final Research Achievements

Multicomponent reactions utilizing helical polymers showing significant chiral amplification phenomena were investigated. We demonstrated that multicomponent reactions using poly(diphenylacetylene) derivatives with high thermal and chemical stabilities, which are reported to show a unique “helicity induction and memory effect”, proceeded in a relatively good yield. Moreover, we discovered that poly(diphenylacetylene) derivatives showed unprecedented anomalous chiral amplification phenomena accompanying helicity inversion and their chiral amplification behavior could be controlled by changing solvents and temperatures.

Academic Significance and Societal Importance of the Research Achievements

三成分以上の基質が反応により一つの生成物へと収束する反応である多成分連結反応は、迅速かつ高効率な分子構築法としてその重要性が注目されている。本研究成果は、らせん高分子に特有の不斉増幅現象を利用することによって、少ない不斉源から効率的な不斉多成分連結反応を実現することにつながる可能性がある。したがって、新しい不斉反応の構築といった学術的な興味だけでなく、創薬化学分野において多様性を指向した強力な合成手段として応用できる可能性を秘めている。また、多様な官能基を有するキラルマテリアルの効率的な合成法としての応用も期待される。

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (6 results)

All 2019 2018 2017

All Journal Article (3 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 3 results) Presentation (3 results)

  • [Journal Article] A Three-State Switchable Chiral Stationary Phase Based on Helicity Control of an Optically Active Poly(phenylacetylene) Derivative by Using Metal Cations in the Solid State2019

    • Author(s)
      Hirose Daisuke、Isobe Asahi、Quinoa Emilio、Freire Felix、Maeda Katsuhiro
    • Journal Title

      Journal of the American Chemical Society

      Volume: 141 Issue: 21 Pages: 8592-8598

    • DOI

      10.1021/jacs.9b03177

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of Amphiphilic Block Copolymers Containing Chiral Polythiophene Chains and Their Micelle Formation and Chiroptical Properties2018

    • Author(s)
      Hirose Daisuke、Nozaki Satoru、Kanoh Shigeyoshi、Maeda Katsuhiro
    • Journal Title

      Polymers

      Volume: 10 Issue: 7 Pages: 718-718

    • DOI

      10.3390/polym10070718

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Multi-component post-polymerization modification reactions of polymers featuring lignin-model compounds2018

    • Author(s)
      Kakuchi Ryohei、Yoshida Satoshi、Sasaki Takasuke、Kanoh Shigeyoshi、Maeda Katsuhiro
    • Journal Title

      Polymer Chemistry

      Volume: 9 Issue: 16 Pages: 2109-2115

    • DOI

      10.1039/c7py01923h

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 側鎖にキラルな置換基を有するポリ(ジフェニルアセチレン)誘導体のらせん形成における非線形効果2018

    • Author(s)
      石橋秀隆、廣瀬大祐、西村達也、井改知幸、前田勝浩
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 光学活性基を有するポリ(ジフェニルアセチレン)誘導体の特異な不斉増幅挙動2018

    • Author(s)
      石橋秀隆、廣瀬大祐、西村達也、井改知幸、前田勝浩
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 多成分連結反応を活用した新規熱応答性高分子の創成2017

    • Author(s)
      佐々木隆祐、覚知亮平、加納重義、前田勝浩
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Research-status Report

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Published: 2017-07-21   Modified: 2020-03-30  

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