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2013 Fiscal Year Final Research Report

Development of Main-chain Polymer of Chiral Organocatalyst and Its Application to Asymmetric Organocatalysis

Research Project

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Project/Area Number 24750103
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Polymer chemistry
Research InstitutionToyohashi University of Technology

Principal Investigator

HARAGUCHI Naoki  豊橋技術科学大学, 工学(系)研究科(研究院), 准教授 (30378260)

Project Period (FY) 2012-04-01 – 2014-03-31
Keywords有機分子触媒 / アミンスルホネート / キラル高分子 / Diels-Alder反応 / イミダゾリジノン / イオン結合 / MacMillan触媒 / イオン交換反応
Research Abstract

Main-chain polymers of chiral organocatalyst with ionic bond have successfully synthesized by the successive aminesulfonate reactions of chiral imidazolidinone dimers with disulfonic acids. These main-chain polymers of chiral organocatalyst polymers showed higher catalytic activity than the corresponding model organocatalyst in the asymmetric Diels-Alder reaction of cyclopentadiene and cinnmaldehyde. These polymeric chiral organocatalyst could be reused several times without loss of the enantioselectivity.

  • Research Products

    (19 results)

All 2014 2013 2012 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (10 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Synthesis of Cinchona Alkaloid-derived Chiral Polymers by Mizoroki-Heck Polymerization and Their Application to Asymmetric Catalysis2014

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

      Macromolecules

      Volume: 47 Pages: 1922-1928

    • DOI

      10.1021/ma5001018

    • Peer Reviewed
  • [Journal Article] Synthesis of chiral quaternary ammonium polymers for asymmetric organocatalysis application2013

    • Author(s)
      Parbhej Ahamed, Md. Aminul Haque, Mikiya Ishimoto, Md. Masud Parvez, Naoki Haraguchi, and Shinichi Itsuno
    • Journal Title

      Tetrahedron

      Volume: 69 Pages: 3978-3983

    • DOI

      10.1016/j.tet.2013.03.018

    • Peer Reviewed
  • [Journal Article] Synthesis of polymer-immobilized TsDPEN ligand and its application in asymmetric transfer hydrogenation of cyclic sulfonimine2013

    • Author(s)
      Haruki Sugie, Yosuke Hashimoto, Naoki Haraguchi, and Shinichi Itsuno
    • Journal Title

      J. Organomet. Chem.

      Volume: 751 Pages: 711-716

    • DOI

      10.1016/j.jorganichem.2013.09.008

    • Peer Reviewed
  • [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: 48 Pages: 4011-4013

    • DOI

      10.1039/C2CC18115K

    • Peer Reviewed
  • [Journal Article] Synthesis of Main-chain Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Using Quaternization Polymerization2012

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

      Molecules

      Volume: 17 Pages: 7569-7583

    • DOI

      10.3390/molecules17067569

    • 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: 10 Pages: 2870-2877

    • DOI

      10.1039/C2OB06909A

    • 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, and Shinichi Itsuno
    • Journal Title

      J. Chinese Chem. Soc.

      Volume: 59 Pages: 815-821

    • DOI

      10.1002/jccs.20110724

    • Peer Reviewed
  • [Presentation] 有機分子触媒組込型キラル高分子の開発と不斉反応への応用2013

    • Author(s)
      原口直樹
    • Organizer
      第145回東海高分子研究会講演会
    • Place of Presentation
      長良川観光ホテル石金
    • Year and Date
      20130927-28
  • [Presentation] キラル有機分子触媒組込型高分子の分子設計と不斉反応への応用2013

    • Author(s)
      原口直樹
    • Organizer
      第62回高分子討論会
    • Place of Presentation
      金沢大学
    • Year and Date
      20130911-13
  • [Presentation] Design and Synthesis of Novel Polymeric Chiral Organocatalysts2013

    • Author(s)
      Naoki Haraguchi
    • Organizer
      1st International Conference on Advanced Molecular Transformation by Organocatalysts
    • Place of Presentation
      Ohtsu Prince Hotel, Shiga, Japan
    • Year and Date
      20130527-28
  • [Presentation] Molecular Design of Polymer-supported Chiral Organocatalyst for Asymmetric Reaction2012

    • Author(s)
      Naoki Haraguchi
    • Organizer
      First Japan-USA Organocatalytic Symposium
    • Place of Presentation
      Hawaii Prince Hotel Waikiki, Hawaii, USA
    • Year and Date
      20121215-18
  • [Presentation] Main-chain chiral polymers as catalyst in asymmetric benzylation of glycine derivative2012

    • Author(s)
      Md. Masud Parvez, Naoki Haraguchi, and Shinichi Itsuno
    • Organizer
      The 9th SPSJ International Polymer Conference (IPC2012)
    • Place of Presentation
      Kobe, Japan
    • Year and Date
      20121211-14
  • [Presentation] 主鎖シンコナアルカロイド四級塩型高分子による不斉アルキル化反応2012

    • Author(s)
      原口直樹, Parbhej Ahamed, Md. Masud Parvez, 伊津野真一
    • Organizer
      第5回有機触媒シンポジウム
    • Place of Presentation
      学習院大学
    • Year and Date
      20121026-27
  • [Presentation] 高分子固定化キラル有機分子触媒の開発2012

    • Author(s)
      原口直樹
    • Organizer
      第1回有機分子触媒若手セミナー
    • Place of Presentation
      ラフォーレ那須
    • Year and Date
      20120908-09
  • [Presentation] Synthesis of main-chain polymers for asymmetric organocatalysis application2012

    • Author(s)
      Naoki Haraguchi, Hitomi Kiyono, Md. Masud Parvez, Parbhej Ahamed, and Shinichi Itsuno
    • Organizer
      Chirality 2012
    • Place of Presentation
      Hilton Fort Worth, Texas, USA
    • Year and Date
      20120610-13
  • [Presentation] Synthesis of Main-chain Polymer of Chiral Imidazolidinone for Asymmetric Diels-Alder Reaction2012

    • Author(s)
      Naoki Haraguchi, Hitomi Kiyono, Aisyah Najwa, and Shinichi Itsuno
    • Organizer
      Symposium on Molecular Chirality ASIA 2012
    • Place of Presentation
      Central Hall Kyushu University School of Medicine, Hakata
    • Year and Date
      20120517-18
  • [Presentation] Cinchona based main-chain polymeric organocatalyst using Mizoroki-Heck coupling reaction and their application to asymmetric reactions2012

    • Author(s)
      Md. Masud Parvez, Naoki Haraguchi, and Shinichi Itsuno
    • Organizer
      Symposium on Molecular Chirality ASIA 2012
    • Place of Presentation
      Central Hall Kyushu University School of Medicine, Hakata
    • Year and Date
      20120517-18
  • [Book] "有機分子触媒の新たな高分子固定化法"月刊ファインケミカル2014年6月号2014

    • Author(s)
      原口直樹, 伊津野真一
  • [Remarks]

    • URL

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

URL: 

Published: 2015-06-25  

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