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2013 Fiscal Year Final Research Report

Synthesis of chiral ionic polymers and their application to asymmetric catalysis

Research Project

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Project/Area Number 23350053
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Polymer chemistry
Research InstitutionToyohashi University of Technology

Principal Investigator

ITSUNO Shinichi  豊橋技術科学大学, 工学(系)研究科(研究院), 教授 (50158755)

Co-Investigator(Kenkyū-buntansha) HARAGUCHI Naoki  豊橋技術科学大学, 大学院・工学研究科, 准教授 (30378260)
Project Period (FY) 2011-04-01 – 2014-03-31
Keywordsイオン結合 / キラル高分子 / 不斉触媒 / 高分子組込み型触媒 / イオン結合型高分子
Research Abstract

The research project involved the synthesis of chiral polymers containing ionic bonds in their main chains and their application to asymmetric catalysis. We have prepared novel type of ionic polymers in which repeating units of the polymers were linked with ionic bonds. Most of the synthetic polymers are covalently bonded chain. We have developed novel type of ionic polymers. These ionic polymers consist of chiral repeating units, which were used as catalysts in asymmetric reactions. They showed excellent catalytic activity in asymmetric reaction. Because of their insolubility, the chiral ionic polymers were readily separated from the reaction mixture and reused many times without any loss of the catalytic activity.

  • Research Products

    (37 results)

All 2014 2013 2012 2011 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (23 results) (of which Invited: 1 results) Book (4 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 Polymerimmobilized TsDPEN Ligand and Its Application in Asymmetric Transfer Hydrogenation of Cyclic Sulfonimine2014

    • Author(s)
      Sugie, H. ; Hashimoto, Y. ; Haraguchi, N. ; Itsuno, S.
    • Journal Title

      J. Organomet. Chem

      Volume: 751 Pages: 711-716

    • DOI

      10.1016/j.jorganichem.2013.09.008

    • Peer Reviewed
  • [Journal Article] Synthesis of Chiral Quaternary Ammonium Polymers for Asymmetric Organocatalysis Application2013

    • Author(s)
      Ahamed, P. ; Haque, M. A. ; Ishimoto, M. ; Parvez, M. M. ; Haraguchi, N. ; Itsuno, S
    • Journal Title

      Tetrahedron

      Volume: 69 Pages: 3978-3983

    • DOI

      10.1016/j.tet.2013.03.018

    • Peer Reviewed
  • [Journal Article] Proline Recognition through CH---Pi Interaction within Crystal Structures of DL-ProlineCalix[4] pyrogallolarene Molecular Complexes2012

    • Author(s)
      Ikuhide Fujisawa, Noriko Harima, Kenji Takagi, Shuichi Hiraoka, Mitsuhiko Shionoya, Kazutaka Murayama, Shinichi Itsuno, Ryo Kato, and Katsuyuki Aoki
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 85 Pages: 1037-1039

    • Peer Reviewed
  • [Journal Article] Design of Main-chain Polymers 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] 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 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] 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
  • [Journal Article] Polymeric Chiral Organocatalysts2011

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

      Polym. Chem

      Volume: 2 Pages: 1942-1949

    • DOI

      10.1039/C1PY00083G

    • Peer Reviewed
  • [Presentation] Asymmetric catalytic activity of quaternary ammonium salts of cinchona alkaloid containing acetylenic moiety2014

    • Author(s)
      Md. Mehadi Hassan, 原口直樹, 伊津野真一
    • Organizer
      日本化学会第94回春季大会
    • Place of Presentation
      名古屋大学
    • Year and Date
      20140327-30
  • [Presentation] スルホンアミド構造を有するシンコニジン四級アンモニウム塩の合成と不斉アルキル化反応(II)2014

    • Author(s)
      山本峻也, 原口直樹, 伊津野真一
    • Organizer
      日本化学会第94回春季大会
    • Place of Presentation
      名古屋大学
    • Year and Date
      20140327-30
  • [Presentation] MacMillan触媒を主鎖骨格に有する高分子触媒の合成と不斉反応への応用2014

    • Author(s)
      濤立晃, 原口直樹, 伊津野真一
    • Organizer
      日本化学会第94回春季大会
    • Place of Presentation
      名古屋大学
    • Year and Date
      20140327-30
  • [Presentation] 主鎖にシンコナアルカロイド二量体を有するキラル高分子の開発と不斉反応への応用(II)2014

    • Author(s)
      黒田到, 原口直樹, 伊津野真一
    • Organizer
      主鎖にシンコナアルカロイド二量体を有するキラル高分子の開発と不斉反応への応用(II)
    • Place of Presentation
      名古屋大学
    • Year and Date
      20140327-30
  • [Presentation] スルホンアミド構造を有するシンコニジン四級アンモニウム塩ダイマーの合成と不斉反応への応用2013

    • Author(s)
      藪崎翔太, 山本峻也, 原口直樹, 伊津野真一
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡大学
    • Year and Date
      20131102-03
    • Invited
  • [Presentation] スルホンアミド構造を有するシンコニジン四級アンモニウム塩の合成と不斉アルキル化反応への応用2013

    • Author(s)
      山本峻也, 原口直樹, 伊津野真一
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡大学
    • Year and Date
      20131102-03
  • [Presentation] MacMillan触媒を主鎖骨格に有するイオン結合型キラル高分子の合成と不斉Diels-Alder反応への応用(IV)2013

    • Author(s)
      竹中渚, Aisyah Najwa, 原口直樹, 伊津野真一
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡大学
    • Year and Date
      20131102-03
  • [Presentation] 主鎖にシンコナアルカロイド二量体を有するキラル高分子の開発と不斉反応への応用2013

    • Author(s)
      黒田到, 原口直樹, 伊津野真一
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都国際会館
    • Year and Date
      20130529-31
  • [Presentation] イオン結合型MacMillan触媒固定化高分子微粒子の合成2013

    • Author(s)
      小林拓真, 原口直樹, 伊津野真一
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都国際会館
    • Year and Date
      20130529-31
  • [Presentation] Synthesis of main-chain chiral polymers of cinchona alkaloid and their application in asymmetric catalysis2013

    • Author(s)
      Md. Masud Parvez, 原口直樹, 伊津野真一
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都国際会館
    • Year and Date
      20130529-31
  • [Presentation] Asymmetric Transfer Hydrogenation of Imines Catalyzed by Amphiphilic Polymer-supported Chiral Catalyst2013

    • Author(s)
      Haraguchi, N. ; Hashimoto, Y. ; Itsuno S.
    • Organizer
      4th UK/Japan Conference in Catalytic Asymmetric Synthesis
    • Place of Presentation
      Sendai International Center, Sendai, Japan
    • Year and Date
      20130419-20
  • [Presentation] Synthesis of main-chain chiral quaternary ammonium salt polymers containing 10, 11-didehydrocinchona alkaloid and their applications to asymmetric reactions2013

    • Author(s)
      Hassan, M. M. ; Haraguchi, N. ; Itsuno S
    • Organizer
      4th UK/Japan Conference in Catalytic Asymmetric Synthesis
    • Place of Presentation
      Sendai International Center, Sendai, Japan
    • Year and Date
      20130419-20
  • [Presentation] スルホンアミド構造を有するシンコニジン四級アンモニウム塩を用いた不斉アルキル化反応2013

    • Author(s)
      山本峻也, 原口直樹, 伊津野真一
    • Organizer
      日本化学会第93回春季大会
    • Place of Presentation
      立命館大学
    • Year and Date
      20130322-25
  • [Presentation] MacMillan触媒骨格を主鎖に有するイオン結合型キラル高分子の合成と不斉Diels-Alder反応への応用(III)2013

    • Author(s)
      Aisyah Najwa , 原口直樹, 伊津野真一
    • Organizer
      日本化学会第93回春季大会
    • Place of Presentation
      立命館大学
    • Year and Date
      20130322-25
  • [Presentation] シリル基およびチオエーテル構造を有するシンコナアルカロイド由来有機分子触媒の合成と不斉反応への応用2013

    • Author(s)
      Md. Robiul Islam, 原口直樹, 伊津野真一
    • Organizer
      日本化学会第93回春季大会
    • Place of Presentation
      立命館大学
    • Year and Date
      20130322-25
  • [Presentation] Asymmetric Catalytic Activity of Ionic Chiral Polymers Synthesized from Disulfonate and Quaternary Ammonium Salt of Cinchona Alkaloid Dimers Containing Acetylenic Moiety2013

    • Author(s)
      Itsuno, S.
    • Organizer
      IGNITE 2013
    • Place of Presentation
      Penang, Malaysia
    • Year and Date
      2013-12-05
  • [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] 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] Polymer design for asymmetric catalyst immobilization2012

    • Author(s)
      Shinichi Itsuno, Yosuke Hashimoto, Haruki Sugie, and Naoki Haraguchi
    • Organizer
      Porous polymer-based systems(EUPOC 2012)
    • Place of Presentation
      Gargnano, Italy
    • Year and Date
      20120603-07
  • [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 Scool of Medicine, Hakata, Japan
    • 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 Scool of Medicine, Hakata, Japan
    • Year and Date
      20120517-18
  • [Presentation] Molecular Design of Main-chain Chiral Quaternary Ammonium Polymers for Asymmetric Catalysis Application2012

    • Author(s)
      Shinichi Itsuno, Md. Masud Parvez, and Naoki Haraguchi
    • Organizer
      14th IUPAC Conference on Polymers and Organic Chemistry (POC2012)
    • Place of Presentation
      The Renaissance Doha City Center Hotel, Doha, Qater
    • Year and Date
      20120106-09
  • [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 (POC2012)
    • Place of Presentation
      The Renaissance Doha City Center Hotel, Doha, Qater
    • Year and Date
      20120106-09
  • [Book] Polymer Catalysts in "Encyclopedia of Polymeric Nanomaterial(Ed. Kobayashi S. ; Mullen, K.)2014

    • Author(s)
      Itsuno, S
    • Publisher
      Springer(in press)
    • URL

      http://www.springer.com/chemistry/polymer+science/book/978-3-642-29647-5

  • [Book] "Supported Organocatalysts" in Science of Synthesis Asymmetric Organocatalysis 2, Maruoka, K. Ed. : Chapter 2. 3. 52011

    • Author(s)
      Shinichi Itsuno and Naoki Haraguchi
    • Total Pages
      673-695
    • Publisher
      Thieme, New York
  • [Book] Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis2011

    • Author(s)
      Shinichi Itsuno
    • Publisher
      Wiley, Singapore
  • [Book] 光学活性化合物の入手, 分析利用法クロマト法有機合成実験法ハンドブック第2版

    • Author(s)
      伊津野真一
    • Publisher
      丸善
  • [Remarks]

    • URL

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

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Published: 2015-06-25  

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