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Development of highly efficient asymmetric synthesis process using simple five-membered heterocycles

Research Project

Project/Area Number 17590010
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

MATSUNAGA Hirofumi  Kumamoto Univ., Graduate School of Medical and Pharmaceutical Sciences, Research Associate, 大学院医学薬学研究部, 助教授 (10274713)

Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2006: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2005: ¥2,400,000 (Direct Cost: ¥2,400,000)
Keywordsroofed / asymmetric synthesis / 1,2-diamines / asymmetric alkylation / asymmetric transfer hydrogenation / iminothioether / asymmetric Diels-Alder reaction / 2-thiazoline / 不斉置換変換反応 / イミノジスルフィド / 2-アミノチオール / アリールイミン
Research Abstract

The aim of this research is to establish the methodology for excellent asymmetric reactions using bicyclic "roofed" 2-airino alcohols, 1,2-diamines and 2-aminothiols and their derivatives, derived from the corresponding tricyclic 2-oxazolidinones, 2-imidazolidinones and 2-thiazolidinones, and they have been proven to be good to excellent chiral ligands for following metal-catalyzed asymmetric reactions:
1) "Roofed" 2-iminothioether-Pd (II) complex-catalyzed asymmetric substitution (alkylation, amination) of allylacetates.
2) "Roofed"2-thiazoline-Cu (II) complex-catalyzed asymmetric Diels-Alder reaction.
3) "Roofed" cis-1,2-diamine-Ru (II) complex-catalyzed asymmetric transfer hydrogenation of ketones and imines.

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • Research Products

    (13 results)

All 2005

All Journal Article (13 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
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Highly efficient asymmetric transfer hydrogenation of ketones catalyzed by chiral 'roofed' cis-diamine-Ru(II) complex2005

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

      Tetrahedron Letters 46

      Pages: 3645-3648

    • NAID

      130006996413

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 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
      2006 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
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Sterically congested "roofed" 2-iminothioethers as new chiral ligands 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
      2006 Final Research Report Summary
  • [Journal Article] Synthetic utility of five- membered heterocycles・chiral functionalization 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
      2006 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 Lett. 46

      Pages: 3645-3648

    • NAID

      130006996413

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Sterically Congested "Roofed" 2-Thiazolines as New Chiral Ligands for Copper(II)-Catalyzed Asymmetric Diel s-Alder Reactions2005

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

      Tetrahedron Lett. 46

      Pages: 4019-4022

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 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
      2006 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
      2006 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.
    • Journal Title

      Tetrahedron Letters 46

      Pages: 3645-3648

    • NAID

      130006996413

    • 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)
      Yamakuchi, M.
    • Journal Title

      Tetrahedron Letters 46

      Pages: 4019-4022

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Sterically congested"roofed"2-iminothioethers as new chiral ligands for palladium-catalyzed asymmetric allylic alkylation2005

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

      Heterocycles 66

      Pages: 135-141

    • Related Report
      2005 Annual Research Report

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Published: 2005-04-01   Modified: 2016-04-21  

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