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Asymmetric reactions controled with moleculary imprinted polymers.

Research Project

Project/Area Number 15590013
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKumamoto University

Principal Investigator

ISHIZUKA Tadao  Kumamoto University, faculty of medical and pharmaceutical Sciences, Associate Professor, 大学院・医学薬学研究部, 助教授 (60176203)

Project Period (FY) 2003 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2005: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2004: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2003: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsMoleculary Imprinting / Asymmetric synthesis / Polymer / Diamine / Amino alcohol / 不斉合成 / 不斉触媒
Research Abstract

Molecularly imprinted polymers were synthesized by use of bicyclic chiral aminoalcohols as template. The difference of affinities between the template molecule and other aminoalcohols to the polymers were detected by HPLC analysis, selective adsorbtion of templete molecule were observed. Moreover, the templete aminoalcohols showed priority in adosorbtion to the imprinted polymer over its enantiomer.
Asymmetric reactions with template molecules as catalysts were examined. Sulfonamides, thiazolines and thioethers with bicyclic skeleton were successfully utilized in hydrogen-transfer reduction of ketones, the Diels-Alder reactions and π-allyl alkylations, respectively. These compounds showed not only high yields and excellent selectiveties but marvelous character that cannot be affected by sterically bulkyness of substrate.
These catalysts might be good templetes of imprinted polymers because of these basic characters and restricted conformations. Further investigations will be needed for application of the imprinted polymers to these asymmetric reactions.

Report

(4 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • 2003 Annual Research Report
  • Research Products

    (18 results)

All 2005 2004

All Journal Article (18 results)

  • [Journal Article] Synthetic utility of five-membered heterocycles-chiral functionalization and applications2005

    • Author(s)
      Matsunaga, H.
    • Journal Title

      Tetrahedron 61

      Pages: 8073-8094

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Highly efficient asymmetric transfer hydrogenetion of ketones catalyzed by chiral 'roofed' cis-diamine-Ru(II) complex2005

    • Author(s)
      Matsunaga, H.
    • Journal Title

      Tetrahedrom Letters 46

      Pages: 3645-3648

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Sterically Congested "Roofed" 2-Thiazolines as New Chiral Ligands for Copper(II)-Catalyzed Asymmetric Diels-Alder Reactions2005

    • Author(s)
      Yamakuchi, M.
    • Journal Title

      Tetrahedron Letters 46

      Pages: 4019-4022

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Asymmetric Ring Opening of meso-Epoxides Catalyzed by the Chiral Phosphine Oxide BINAPO2005

    • Author(s)
      Tokuoka, E.
    • Journal Title

      Tetrahedron : Asymmetry 16

      Pages: 2391-2392

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Sterically congested "roofed" 2-iminothioethers as new chiralligands for palladium-catalyzed asymmetric allylic alkylation2005

    • Author(s)
      Tokuda, R.
    • Journal Title

      Heterocycles 66

      Pages: 135-141

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthetic utility of five-membered heterocycles chiral functionaliz-ation and applications2005

    • Author(s)
      Matsunaga, H. et al.
    • Journal Title

      Tetrahedron 61

      Pages: 8073-8094

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Highly efficient asymmetric transfer hydrogenation of ketones catalyzed by chiral 'roofed' cis-diamine-Ru(II) complex2005

    • Author(s)
      Matsunaga, H. et al.
    • Journal Title

      Tetrahedron Letters 46

      Pages: 3645-3648

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Sterically Congested "Roofed" 2-Thiazolines as New Chiral Ligands for Copper(II)-Catalyzed Asymmetric Diels-Alder Reactions2005

    • Author(s)
      Yamakuchi M., et al.
    • Journal Title

      Tetrahedron Letters 46

      Pages: 3645-3648

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Asymmetric Ring Opening of meso-Epoxides Catalyzed by the Chiral Phosphine Oxide BINAPO2005

    • Author(s)
      Tokuoka, E. et al.
    • Journal Title

      Tetrahedron : Asymmetry 16

      Pages: 2391-2392

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Sterically congested "roofed" 2-iminothioethers as new chiral ligands for palladium-catalyzed asymmetric allylic alkylation2005

    • Author(s)
      Tokuda, R. et al.
    • Journal Title

      Heterocycles 66

      Pages: 135-141

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Sterically Congested "Roofed" 2-Iminothioethers as New Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation2005

    • Author(s)
      Ryoh Tokuda
    • Journal Title

      Heterocyles 66

      Pages: 135-141

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Sterically congested 'roofed' 2-thiazolines as new chiral ligands for copper(II)-catalyzed asymmetric Diels-Alder reactions2005

    • Author(s)
      Manabu Yamakuchi
    • Journal Title

      Tetrahedron Letters 46

      Pages: 4019-4022

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Highly efficient asymmetric transfer hydrogenation of ketones catalyzed by chiral 'roofed' cis-diamine-Ru(II) complex2005

    • Author(s)
      Hirofumi Matsunaga
    • Journal Title

      Tetrahedron Letters 46

      Pages: 3645-3648

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Chiral phosphine oxide BINAPO as a catalyst for enantioselective allylation of aldehydes with allyltrichlorosilanes2005

    • Author(s)
      Makoto Nakajima
    • Journal Title

      Tetrahedron Letters 46

      Pages: 157-159

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Catalytic dissymmetrization of meso-2-imidazolidinones : alternative route to chiral cynthons for 1,2-diamines2004

    • Author(s)
      Ishizuka, T.
    • Journal Title

      Tetrahedron Letters 45

      Pages: 9327-9330

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Catalytic dissymmetrization of meso-2-imidazolidinones : alternative route to chiral cynthons for 1,2-diamines2004

    • Author(s)
      Ishizuka, T. et al.
    • Journal Title

      Tetrahedron Letters 45

      Pages: 9327-9330

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Enantioselective Aldol Reaction of Trimethoxysilyl Enol Ether Catalyzed by Lithium Binaphtholate2004

    • Author(s)
      Makoto Nakajima
    • Journal Title

      Organic Letters 6

      Pages: 3763-3765

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Catalytic dissymmetrization of meso-2-imidazolidinones : alternative route to chiral synthons for 1,2-diamines2004

    • Author(s)
      Tadao Ishizuka
    • Journal Title

      Tetrahedron Letters 45

      Pages: 9327-9330

    • Related Report
      2004 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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