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Immobilization of Chiral Organocatalyst onto Polymer through Ionic Bonding

Research Project

Project/Area Number 22750105
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Polymer chemistry
Research InstitutionToyohashi University of Technology

Principal Investigator

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

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2011: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2010: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywords有機分子触媒 / 有機触媒 / 高分子触媒 / 不斉触媒 / 高分子固定化 / 不斉反応 / イオン結合 / イオン交換反応 / アルキル化反応 / Diels-Alder反応 / MacMillan触媒 / 四級アンモニウム塩 / スルホン酸塩
Research Abstract

Ionically polymer-supported chiral organ catalyst was successfully prepared by the ion exchange reaction of a sulfonated polymer and a chiral organ catalyst. The methodology is one of the efficient immobilization methods because chiral organ catalyst with ammonium, amine, or iminium salt can be immobilized onto polymer rapidly and quantitatively. The catalytic activity of ionically polymer-supported chiral organ catalyst in asymmetric reactions was found to be equal or superior to that of model chiral catalyst.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (39 results)

All 2012 2011 2010 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (21 results) Book (4 results) Remarks (3 results)

  • [Journal Article] Design of Main-chain Polymer of Chiral Imidazolidinone for Asymmetric Organocatalysis Application2012

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

      Chem. Commun

      Volume: (in press) Issue: 33 Pages: 48-48

    • DOI

      10.1039/c2cc18115k

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Design of Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Application2012

    • Author(s)
      Md. Masud Parvez, Naoki Haraguchi, and Shinichi Itsuno
    • Journal Title

      Org. Biomol. Chem

      Volume: (in press) Issue: 14 Pages: 9-9

    • DOI

      10.1039/c2ob06909a

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Chiral Ionic Polymers Containing Quaternary Ammonium Sulfonate structure and their Catalytic Activity in Asymmetric Alkylation2012

    • Author(s)
      Md.Masud Parvez, Md.Abdus Salam, Naoki Haraguchi, Shinichi Itsuno
    • Journal Title

      J.Chinese Chem.Soc.

      Volume: 59(In Press)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Polymeric Chiral Organocatalysts2011

    • Author(s)
      Naoki Haraguchi, Md. Masud Parvez, and Shinichi Itsuno
    • Journal Title

      Polym. Chem

      Volume: 2 Issue: 9 Pages: 1942-1949

    • DOI

      10.1039/c1py00083g

    • Related Report
      2011 Annual Research Report 2011 Final Research Report
    • 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, and Naoki Haraguchi
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 132 Issue: 9 Pages: 2864-2865

    • DOI

      10.1021/ja909972d

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Novel Polymer-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, and Shinichi Itsuno
    • Journal Title

      Tetrahedron Lett

      Volume: 51 Issue: 8 Pages: 1205-1208

    • DOI

      10.1016/j.tetlet.2009.12.088

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [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

    • Related Report
      2010 Annual Research Report
    • 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

    • NAID

      10027176852

    • Related Report
      2010 Annual Research Report
    • 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

    • Related Report
      2010 Annual Research Report
    • 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

    • Related Report
      2010 Annual Research Report
    • 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

    • NAID

      10026584604

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] MacMillan触媒を主鎖骨格に有するイオン結合型高分子キラル有機分子触媒を用いた不斉Diels-Alder反応2012

    • Author(s)
      原口直樹、清野仁美、竹村由、伊津野真一
    • Organizer
      日本化学会第92回春季大会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2011 Final Research Report
  • [Presentation] Development of Novel Polymer-supported MacMillan Catalysts with Ionic Bond for Asymmetric Reaction2012

    • Author(s)
      Naoki Haraguchi, Hitomi Kiyono, Yu Takemura, Masahiro Kaneko, and Shinichi Itsuno
    • Organizer
      14th IUPAC Conference on Polymers and Organic Chemistry
    • Place of Presentation
      The Renaissance Doha City Center Hotel
    • Related Report
      2011 Final Research Report
  • [Presentation] Molecular Design of Main-chain Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Application2012

    • Author(s)
      Shinichi Itsuno, Md.Masud Parvez, Naoki Haraguchi
    • Organizer
      14th IUPAC Conference on Polymers and Organic Chemistry (POC2012)
    • Place of Presentation
      Doha, Qater
    • Related Report
      2011 Annual Research Report
  • [Presentation] Development of Novel Polymer-supported MacMillan Catalysts with Ionic Bond for Asymmetric Reaction2012

    • Author(s)
      Naoki Haraguchi, Hitomi Kiyono, Yu Takemura, Masahiro Kaneko, Shinichi Itsuno
    • Organizer
      14th IUPAC Conference on Polymers and Organic Chemistry (POC2012)
    • Place of Presentation
      Doha, Qater
    • Related Report
      2011 Annual Research Report
  • [Presentation] キラル有機触媒を主鎖に含むイオン結合型高分子の開発と不斉反応への応用2011

    • Author(s)
      原口直樹、清野仁美、竹村由、伊津野真一
    • Organizer
      第4回有機触媒シンポジウム
    • Place of Presentation
      東京理科大学
    • Year and Date
      2011-09-17
    • Related Report
      2011 Final Research Report
  • [Presentation] イオン結合によりMacMillan触媒を組み込んだ高分子不斉触媒の合成II2011

    • Author(s)
      金子昌広、原口直樹、伊津野真一
    • Organizer
      第60回高分子学会年次大会
    • Place of Presentation
      大阪国際会議場
    • Related Report
      2011 Final Research Report
  • [Presentation] イオン結合による高分子固定化型キラル有機触媒の開発2011

    • Author(s)
      原口直樹、伊津野真一
    • Organizer
      Symposium on Molecular Chirality 2011
    • Place of Presentation
      東京工業大学
    • Related Report
      2011 Final Research Report
  • [Presentation] Facile immobilization of MacMillan catalyst for asymmetric Diels-Alder reaction2011

    • Author(s)
      Naoki Haraguchi, Yu Takemura, Masahiro Kaneko, and Shinichi Itsuno
    • Organizer
      ACS 241st National Meeting, Anaheim
    • Place of Presentation
      CA, USA
    • Related Report
      2011 Final Research Report
  • [Presentation] イオン結合を利用した高分子MacMillan触媒の合成と不斉Diels-Alder反応への応用2011

    • Author(s)
      竹村由、原口直樹、伊津野真一
    • Organizer
      日本化学会第91春季大会
    • Place of Presentation
      神奈川大学
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis of Optically Active Quaternary Ammonium Polymers and Their Application in Asymmetric Catalysis2011

    • Author(s)
      Shinichi Itsuno, Md.Masud Parvez, Naoki Haraguchi
    • Organizer
      2nd International Symposium Frontiers in Polymer Science
    • Place of Presentation
      Lyon, France(招待講演)
    • Related Report
      2011 Annual Research Report
  • [Presentation] Molecular Design of Optically Active Quaternary Ammonium Polvmers and Their Application in Asymmetric Catalysis2011

    • Author(s)
      Shinichi Itsuno, Md.Masud Parvez, Naoki Haraguchi
    • Organizer
      22nd International Symposium : Synthesis in Organic Chemistry
    • Place of Presentation
      UK(招待講演)
    • Related Report
      2011 Annual Research Report
  • [Presentation] Main-chain chiral ionic polymers in asymmetric synthesis2011

    • Author(s)
      Md.Masud Parvez, Naoki Haraguchi, Shinichi Itsuno
    • Organizer
      3rd International Symposium on Network Polymers (Symposium Baekeland2011)
    • Place of Presentation
      Toyohashi, Japan
    • Related Report
      2011 Annual Research Report
  • [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
    • Related Report
      2010 Annual Research Report
  • [Presentation] イオン結合を用いた高分子固定化キラル有機触媒の合成と応用2010

    • Author(s)
      原口直樹、伊津野真一
    • Organizer
      第3回有機触媒シンポジウム
    • Place of Presentation
      東北大学
    • Year and Date
      2010-09-22
    • Related Report
      2011 Final Research Report
  • [Presentation] Polymer-supported chiral imidazolidinone organocatalysts for asymmetric Diels-Alder reaction2010

    • Author(s)
      Naoki Haraguchi, Yu Takemura, Masahiro Kaneko, and Shinichi Itsuno
    • Organizer
      The 6th IUPAC International Symposium on Novel Materials and their Synthesis(NMS-VI)
    • Place of Presentation
      Wuhan, China
    • Related Report
      2011 Final Research Report
  • [Presentation] Synthesis of Novel Polymer-supported Catalyst Using MacMillan Catalyst by Ionic Bond2010

    • Author(s)
      金子昌広、原口直樹、伊津野真一
    • Organizer
      第59回高分子学会年次大会
    • Place of Presentation
      パシフィコ横浜
    • Related Report
      2011 Final Research Report
  • [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
    • Related Report
      2010 Annual Research Report
  • [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)
    • Related Report
      2010 Annual Research Report
  • [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
    • Related Report
      2010 Annual Research Report
  • [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)
    • Related Report
      2010 Annual Research Report
  • [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)
    • Related Report
      2010 Annual Research Report
  • [Book] Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis2011

    • Author(s)
      Naoki Haraguchi and Shinichi Itsuno
    • Publisher
      Itsuno, S. Ed.
    • Related Report
      2011 Final Research Report
  • [Book] Science of Synthesis(Maruoka, K. Ed)2011

    • Author(s)
      Shinichi Itsuno and Naoki Haraguchi
    • Related Report
      2011 Final Research Report
  • [Book] Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis2011

    • Author(s)
      Naoki Haraguchi, Shinichi Itsuno
    • Publisher
      Wiley
    • Related Report
      2011 Annual Research Report
  • [Book] Asymmetric Organocatalysis 2 in Science of Synthesis2011

    • Author(s)
      Shinichi Itsuno, Naoki Haraguchi
    • Publisher
      Thieme
    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.ens.tut.ac.jp/chiral/

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

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

    • Related Report
      2010 Annual Research Report

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Published: 2010-08-23   Modified: 2016-04-21  

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