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Asymmetric Automultiplication of Chiral Compounds by Asymmetric Autocatalytic Reaction

Research Project

Project/Area Number 07454168
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionScience University of Tokyo

Principal Investigator

SOAI Kenso  Science University of Tokyo, Faculty of Science, Professor, 理学部, 教授 (90147504)

Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥7,700,000 (Direct Cost: ¥7,700,000)
Fiscal Year 1996: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1995: ¥4,800,000 (Direct Cost: ¥4,800,000)
KeywordsAsymmetric autocatalysis / Dialkylzinc / Asymmetric automultiplication / Asymmetric replication / Pyrimidyl alkanol / Quinolyl alkanol / Asymmetric synthesis / 自己増殖 / 不斉自己触媒反応 / 不斉アルキル化反応 / ピリミジルアルコール / キノリルアルコール
Research Abstract

Asymmetric autocatalytic reaction of 2-methyl-1- (5-pyrimidyl) -1-propanol (1) was examined. (S) -1 with high e.e.worked as an asymmetric autocatalysis in the reaction of pyrimidine-5-carbaldehyde and diisopropylzinc to afford (S) -1 with high e.e. When (S) -1 with low e.e.was employed as an asymmetric autocatalyst, the newly formed (S) -1 had an higher e.e. By using the newly formed (S) -1 as the asymmetric autocatalyst for the next reaction, the e.e. of (S) -1 reached 90%e.e. Quinolyl alkanol is also an asymmetric autocatalysis to afford itself with 94% e.e.in the reaction of quinoline-3-carbaldehyde and diisopropylzinc.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (33 results)

All Other

All Publications (33 results)

  • [Publications] K.Soai: "Asymmetric Synthesis of Chiral Diols by the Catalytic Enantioselective Dialkylation of Tere-,Iso-,and Phthalaldehydes and by a Catalytic Enantioselective Autoinductive Reaction." Tetrahedron. 52. 13355-13362 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Enantioselective Synthesis of Chiral 5-Carbamoyl-3-pyridyl Alcohols by Asymmetric Autocatalytic Reaction." Tetrahedron Lett.37. 8783-8786 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "One-pot Asymmetric Autocatalytic Reaction with Remarkable Amplification of Enantiomeric Excess." Tetrahedron:Asymmetry. 8. 1717-1719 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Asymmetric Synthesis of Various Chiral 5-Pyrimidylalkanols by the Enantioselective Alkylation of Pyrimidine-5-carbaldehydes with Dialkylzincs in the Presence of Chiral Amino Alcohols" Heterocycles. 46. 235-240 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Soai: "Design of Chiral Catalysis and Asymmetric Autocatalysis for the Enantioselective Additions of Organozinc Reagents" Yuki Gosei Kagaku Kyokaishi. 55. 994-1005 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Soai: "Asymmetric Autocatalysis and Amplification of Enantiomeric Excess of a Chiral Molecule." Nature(London). 378. 767-768 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidylalcohol." J.Am.Chem.Soc.118. 471-472 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Highly Enantioselective Synthesis of a Chiral 3-Quinolylalkanol by an Asymmetric Autocatalytic Reaction." Chem.Commun.751-752 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Asymmetric Autocatalytic Reaction of 3-Quinolylalkanol with Amplification of Enantiomeric Excess." Chem.Commun.1235-1236 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Soai: "Asymmetric Reactions in which Products Participate.New Development of Asymmetric Autocatalytic Reaction." Kagaku. 51. 600-601 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Chiral Molecule which automultiplies.Development of Highly Enantioselective Autocatalytic Reaction." SUT Bulletin. 13(10). 36-41 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Soai: "Asymmetric Autocatalysis and Amplification of Enantiomeric Excess of a Chiral Molecule." Nature (London). 378. 767-768 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidylalcohol." J.Am.Chem.Soc.118. 471-472 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Highly Enantioselective Synthesis of a Chiral 3-Quinolylalkanol by an Asymmetric Autocatalytic Reaction." Chem.Commun.751-752 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Asymmetric Autocatalytic Reaction of 3-Quinolylalkanol with Amplification of Enantiomeric Excess." Chem.Commun.1235-1236 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Soai: "Asymmetric Reactions in which Products Participate. New Development of Asymmetric Autocatalytic Reaction." Kagaku. 51. 600-601 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Chiral Molecule which automultiplies. Development of Highly Enantioselective Autocatalytic Reaction." SUT Bulletin. 13. 36-41 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Soai: "Asymmetric Synthesis of Chiral Diols by the Catalytic Enantioselective Dialkylation of Tere-, Iso-, and Phthalaldehydes and by a Catalytic Enantioselective Autoinductive Reaction" Tetrahedron. 52. 13355-13362 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Enentioselective Synthesis of Chiral 5-Carbamoyl-3-pyridyl Alcohols by Asymmetric Autocatalytic Reaction." Tetrahedron Lett.37. 8783-8786 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "One-pot Asymmetric Autocatalytic Reaction with Remarkable Amplification of Enantiomeric Excess." Tetrahedron : Asymmetry. 8. 1717-1719 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shibata: "Asymmetric Synthesis of Various Chiral 5-Pyrimidylalkanols by the Enantioselective Alkylation of Pyrimidine-5-carbaldehydes with Dialkylzincs in the Presence of Chiral Amino Alcohols." Heterocycles. 46. 235-240 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Soai: "Design of Chiral Catalysis and Asymmetric Autocatalysis for the Enantioselective Additions of Organosinc Reagents." Yuki Gosei Kagaku Kyokaishi. 55. 994-1005 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Soai: "Asymmetric Autocatalysis and Amplification of Enantiomeric Excess of a Chiral Molecule." Nature (London). 378. 767-768 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] T.Shibata: "Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidylalcohol." J.Am.Chem.Soc.118. 471-472 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] T.Shibata: "Highly Enantioselective Synthesis of a Chiral 3-Quinolylalkanol by an Asymmetric Autocatalytic Reaction." Chem.Commun.751-752 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] T.Shibata: "Asymmetric Autocatalytic Reaction of 3-Quinolylalkanol with Amplification of Enantiomeric Excess." Chem.Commun.1235-1236 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Soai: "Asymmetric Reactions in which Products Participate. New Development of Asymmetric Autocatalytic Reaction." Kagaku. 51. 600-601 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] T.Shibata: "Chiral Molecule which automultiplies. Development of Highly Enantioselective Autocatalytic Reaction." SUT Bulletin. 13(10). 36-41 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Soai: "Asymmetric Synthesis of Chiral Diols by the Catalytic Enantioselective Dialkylation of Tere-, Iso-,and Phthalaldehydes and by a Catalytic Enantioselective Autoinductive Reaction." Tetrahedron. 52. 13355-13362 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] T.Shibata: "Enantioselective Synthesis of Chiral 5-Carbamoyl-3-pyridyl Alcohols by Asymmetric Autocatalytic Reaction." Tetrahedron Lett.37. 8783-8786 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] そ合: "Asymmetric Autocatalysis and Amplification of Enantiomeric Excess of a chiral Mdecule" Nature. 378. 767-768 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 柴田,そ合: "Highly Enantioselective Cataly Asymmetric Auto multiplication of Chiral Ryimidyl Alcohol" J. Am. Chem, Soc.118. 471-472 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] 柴田,そ合: "Highly Enantioselective Synthesis of a chiral 3-Quinolylalkanol by an Asymmetric Autocatalytic Reaction" J. Chem. Soc, Chem. Commun.(印刷中). (1996)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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