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Enantioselective Reaction of Diketene to Aldehydes Promoted by Chiral Titanium Complexes

Research Project

Project/Area Number 06640690
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionYamaguchi University

Principal Investigator

HAYASHI Masahiko  Yamaguchi University, Faculty of Science, Associate professor, 理学部, 助教授 (60192704)

Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 1995: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1994: ¥2,000,000 (Direct Cost: ¥2,000,000)
Keywordstitanum catalyst / Schiff base / diketene / optically active / enantioselectivity / 不斉 / キラル / チタン / 触媒 / エナンチオ選択的反応
Research Abstract

Optically Active 5-hydroxy-3-oxoesters can be converted into 6-substituted 4-hydroxy lactones which are common structural components of compactin and mevinolin known as inhibitors of 3-hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) reductase. W e recently succeeded in the highly efficient preparation of optically active 5-hydroxy-3-oxoesters by enantioselective reaction of diketene with aldehydes promoted by novel chiral Schiff basetitanium alkoxide complexes. This new procedure provides an efficient method for the synthesis of optically active 5-hydroxy-3-oxoesters in up to 92% enantiomeric excess (ee).

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] M. Hayashi: "Novel Enantioselective Reaction of Diketene with Aldehydes Promoted by Chiral Schiff Base-Titanium Alkoxide Complex" J. Chem. Soc., Chem. Commun.341-342 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M. Hayashi: "Novel Asymmetric Ring-opening Reactions of Symmetrical N-Acyl-aziridines with Arenethiols Catalyzed by Chiral Tartrate-Diethylzinc Complexes" J. Chem. Soc., Chem. Commun.2699-2700 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M. Hayashi: "Reduction of α-Trialkylsiloxy Nitriles with Diisobutylaluminium Hydride (DIBAH) : A Facile Preparation of α-Trialkylsiloxy Aldehydes and their Derivatives" Tetrahedron. 50. 2821-2830 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M. Hayashi: "Asymmetric Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron. 50. 4385-4398 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M. Hayashi: "Highly Efficient Preparation of Optically Active 5-Hydroxy-3-oxo-esters by Enantioselective Reaction of Diketene with Aldehydes Promoted by Novel Chiral Schiff Base-Titanium Alkoxide Complexes" Trtrahedron Asymmetry. 6. 1833-1836 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M. Hayashi: "Enantioselective Synthesis of (3S, 5R, 6E, 8E) -Deca-6, 8-dien-1, 3, 5-triol a New Metabolite from Streptomyces Fimbriatus via Asymmetric Reaction of Diketene with 2, 4-Hexadienal Promoted by Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron Asymmetry. 6. 2511-2516 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Hayashi: "Novel Enantioselective Reaction of Diketene with Aldehydes Promoted by Chiral Schiff Base-Tianium Alkoxide Complex" J.Chem.Soc., Chem.Commum.341-342 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Hayashi: "Novel Asymmetric Ring-opening Reactions of Symmetrical N-Acyl-aziridines with Arenethiols Catalyzed by Chiral Tartrate-Diethylzinc Complexes" J.Chem.Soc., Chem.Commum.2699-2700 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Hayashi: "Reduction of alpha-Trialkylsiloxy Nitriles with Diisobutylaluminium Hydride (DIBAH) : A Facile Preparation of alpha-Trialkylsiloxy Aldehydes and their Derivatives" Tetrahedron. 50. 2821-2830 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Hayashi: "Asymmetric Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron. 50. 4385-4398 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Hayashi: "Highly Efficient Preparation of Optically Active 5-Hydroxy-3-oxo-esters by Enantioselective Reaction of Diketene with Aldehydes Promoted by Novel Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron Asynmetry. 6. 1833-1836 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Hayashi: "Enantioselective Synthesis of (3S,5R,6E,8E) -Deca-6,8-dien-1,3,5-triol, a New Metabolite from Streptomyces Fimbriatus via Asymmetric Reaction of Diketene with 2,4-Hexadienal Promoted by Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron Asymmetry. 6. 2511-2516 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Hayashi: "Novel Enantioselective Reaction of Diketene with Aldehydes Promoted by Chiral Schiff Base-Titanium Alkoxide Complex" J.Chem.Soc.,Chem.Commun.341-342 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Hayashi: "Novel Asymmetric Ring-opening Reactions of Symmetrical N-Acylaziridenes with Arenethiols Catalyzed by Chiral Tartrate-Diethylzino Complexes" J.Chem.Soc.,Chem.Commun.2699-2700 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Hayashi: "Reduction of α-Trialkylsiloxy Nitriles with Diisobutylaluminium Hydride A Facile Preparation of α-Trialkylsiloxy Aldehydes and their Derivatives" Tetrahedron. 50. 2821-2830 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Hayashi: "Asymmetric Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron. 50. 4385-4398 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Hayashi: "Highly Efficient Preparation of Optically Active 5-Hydroxy-3-oxoesters by Enantioselective Reaction of Diketene with Aldehydes Promoted by Novel Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron Asymmetry. 6. 1833-1836 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Hayashi: "Enantioselective Synthesis of (3S,5R,6E,8E) -Deca-6,8-dien-1,3,5-triol,a New Metabolite from Streptomyces Fimbriatus via Asymmetric Reaction of Diketene with 2,4-Hexadienal Promoted by Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron Asymmetry. 6. 2511-2516 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Hayashi: "Enantioselective Trimethylsilylcyanation of Some Aldehydes Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes." J.Org.Chem.58. 1515-1522 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Hayashi: "Novel Enantioselective Reaction of Diketene with Some Aldehydes Promoted by Chiral Schiff Base-Titanium Alkoxide Complex." J.Chem.Soc,.Chem.Commun.341-342 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Hayashi: "Novel Asymmetric Ring-opening Reactions of SymmetricalN-Acylaziridines with Arenethiols Catalyzed by Chiral Dialkyl Tartrate--Diethylzinc Complexes." J.Chem.Soc,.Chem.Commun.2699-2670 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Hayashi: "Reduction of α-Trialkylsiloxy Nitriles with Diisobutylaluminium Hydride (DIBAH): A Facile Preparation of α-Trialkylsiloxy aldehydes and their Derivatives." Tetrahedron. 50. 2821-2830 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Hayashi: "Asymmetric Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Schiff Base--Titanium Alkoxide Complexes." Tetrahedron. 50. 4385-4398 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 林 昌彦: "光学活性シッフ塩基-チタンアルコキシド触媒を用いた不斉炭素-炭素結合生成反応" 有機合成化学協会誌. 52. 488-497 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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