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2010 Fiscal Year Annual Research Report

イオン結合による不斉有機分子触媒の高分子固定化法の開発

Research Project

Project/Area Number 22750105
Research InstitutionToyohashi University of Technology

Principal Investigator

原口 直樹  豊橋技術科学大学, 大学院・工学研究科, 助教 (30378260)

Keywords有機分子触媒 / イオン結合 / 高分子固定化 / 不斉反応 / 不斉触媒 / 四級アンモニウム塩 / スルホン酸塩 / イオン交換反応
Research Abstract

アニオン性官能基を有する高分子担体と光学活性第四級アンモニウム塩構造を有する有機分子触媒のイオン交換反応により、有機分子触媒をイオン結合を介した高分子上への固定化を行い、有機分子触媒の簡便かつ効率的な高分子固定化法の開発を行った。スルホン酸塩やカルボン酸塩を有するモノマー、コモノマー、架橋モノマーに親水性、疎水性官能基を導入したスチレン誘導体、(メタ)アクリル酸エステル類、アクリルアミド類を用い、ラジカル溶液重合により、アニオン性官能基を有する固定化用高分子を合成した。ポリマー構造(直鎖型、架橋型)、親水性-疎水性バランス(疎水性、親水性、両親媒性)や架橋度、アニオン性官能基含有量を変えた固定化用高分子を合成し、シンコニジン四級塩、丸岡触媒、キラルイミダゾリジノン塩やチオウレア部位を有するイミニウム塩の反応を行った。反応は副反応無く、定量的に進行し、特にスルホン酸四級アンモニウム塩におけるイオン結合は酸性、塩基性、中性の幅広い範囲において安定なイオン結合を形成することを見出した。本研究より、カチオン性官能基を有する有機分子触媒がイオン結合を介して高分子上に簡便かつ定量的に固定化できることが見出された。また、アニオン性官能基を有する化合物はカチオン性官能基を有する固定化用高分子により、高分子上への固定化が可能であることを明らかとし、イオン性有機分子触媒の高分子固定化法の新たな方法の一つを確立した。

  • Research Products

    (12 results)

All 2011 2010 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (6 results) Remarks (1 results)

  • [Journal Article] Novel Polym er-supported Organocatalyst via Ion Exchange Reaction : Facile immobilization of Chiral Imidazolidin-4-one and Its Application to Diels-Alder Reaction2010

    • Author(s)
      Naoki Haraguchi, Yu Takemura, Shinichi Itsuno
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 1205-1208

    • Peer Reviewed
  • [Journal Article] Designing Chiral Quaternary Ammonium Polymers : Novel Type of Polymeric Catalyst for Asymmetric Alkylation Reaction2010

    • Author(s)
      Shinichi Itsuno, Devproshad, K.Paul, Mikiya Ishimoto, Naoki Haraguchi
    • Journal Title

      Chem.Lett.

      Volume: 39 Pages: 86-87

    • Peer Reviewed
  • [Journal Article] Main-Chain Ionic Chiral Polymers : Synthesis of Optically Active Quaternary Ammonium Sulfonate Polymers and Their Application in Asymmetric Catalysis2010

    • Author(s)
      Shinichi Itsuno, Devproshad K.Paul, M.A.Salam, Naoki Haraguchi
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 2864-2865

    • Peer Reviewed
  • [Journal Article] Synthesis of Polymer Microspheres Functionalized with Chiral Ligand by Precipitation Polymerization and Their Application to Asymmetric Transfer Hydrogenation2010

    • Author(s)
      Naoki Haraguchi, Akihiro Nishiyama, Shinichi Itsuno
    • Journal Title

      J.Polym.Sci.Part A : Polym.Chem.

      Volume: 48 Pages: 3340-3349

    • Peer Reviewed
  • [Journal Article] Synthesis of Polymer-supported Chiral Catalyst and Its Application to Asymmetric Reaction2010

    • Author(s)
      Naoki Haraguchi
    • Journal Title

      Kobunshi Ronbunshu

      Volume: 67 Pages: 447-464

    • Peer Reviewed
  • [Presentation] Facile immobilization of MacMillan catalyst for asymmetric Diels-Alder reaction2011

    • Author(s)
      Naoki Haraguchi, Yu Takemura, Masahiro Kaneko, Shinichi Itsuno
    • Organizer
      ACS 241st National Meeting
    • Place of Presentation
      Anaheim, CA, USA
    • Year and Date
      20110327-20110331
  • [Presentation] Polymer-supported chiral imidazolidinone organocatalysts for asymmetric Diels-Alder reaction2010

    • Author(s)
      Naoki Haraguchi, Yu Takemura, Masahiro Kaneko, Shinichi Itsuno
    • Organizer
      the 20th International Symposium on Fine Chemistry and Functional Polymers (FCFP-XX)
    • Place of Presentation
      Wuhan, China(招待講演)
    • Year and Date
      20101010-20101014
  • [Presentation] Polymer-supported chiral imidazolidinone organocatalysts for asymmetric Diels-Alder reaction2010

    • Author(s)
      Naoki Haraguchi, Yu Takemura, Masahiro Kaneko, Shinichi Itsuno
    • Organizer
      the 6th IUPAC International Symposium on Novel Materials and their Synthesis (NMS-VI)
    • Place of Presentation
      Wuhan, China(招待講演)
    • Year and Date
      20101010-20101014
  • [Presentation] Benign Polymeric Organocatalyst : Synthesis of Chiral Quaternary Ammonium Salt Polymers and Their Use in Asymmetric Catalysis2010

    • Author(s)
      Shinichi Itsuno, Naoki Haraguchi
    • Organizer
      3rd International Conference on Green Chemistry
    • Place of Presentation
      Ontario, Canada
    • Year and Date
      20100815-20100818
  • [Presentation] Synthesis of Optically Active Quaternary Ammonium Polymers and Their Application in Asymmetric Catalysis2010

    • Author(s)
      Shinichi Itsuno, Naoki Haraguchi
    • Organizer
      22nd International Symposium on Chirality (ISCD-22)
    • Place of Presentation
      Sapporo, Japan(招待講演)
    • Year and Date
      20100713-20100715
  • [Presentation] Synthesis of Optically Active Quaternary Ammonium Polymers and Their Application in Asymmetric Catalysis2010

    • Author(s)
      Shinichi Itsuno, Naoki Haraguchi
    • Organizer
      Molecular Chirality 2010
    • Place of Presentation
      Sapporo, Japan
    • Year and Date
      20100711-20100712
  • [Remarks]

    • URL

      http://www.tutms.tut.ac.jp/~haraguchi/

URL: 

Published: 2013-06-26  

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