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1994 Fiscal Year Final Research Report Summary

DEVELOPMENT OF NEW ASYMMETRIC REACTIONS BASED ON CONFORMATIONALY FIXED CYCLOALKANE-POLYOLS.

Research Project

Project/Area Number 05671755
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

SUEMUNE Hiroshi  KYUSHU UNIVERSITY,FACULTY OF PHARMACEUTICAL SCIENCES,ASSISTANT PROFESSOR, 薬学部, 助手 (20095897)

Project Period (FY) 1993 – 1994
KeywordsAsymmetric synthesis / Asymmetric reaction / Configuration / Chiral cyclic diol / Chiral enol ether / Chelation
Research Abstract

Based on our previous study for preparation of enantiomerically pure cycloalkane-1,2-diols by using enzymatic procedure, several asymmetric reactions have been developed in this research project.
1)A new method for asymmetric construction of a quatemary carbon and its application to the synthesis of spiro-cyclic compound have been developed by using cycloalkane-1,2-diols as a chiral auxiliary.
2)New types of asymmetric reactions have been developed by using "chiral enol ether" as a key intermediate : Two kinds of asymmetric Michael reaciton ; Asymmetric oxidation of beta-keto esters ; Chiral induction to meso-cyclic 1,2-diol.
3)Asymmetric spiro-cyclization has been developed by using chiral cycloalkane-1,2-diol as a chiral sorce.

  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] T.Ogawa: "Synthetic Approach to 1,3-Polymethy Function Based on Diastereoselective Conjugate Addition." Chem.Pharm.Bull.41. 1652-1654 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Kato: "New Type of Asymmetric Double Michael Reaction Induced by Chiral Acetal." Tetrahedron Lett.34. 4979-4980 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Suemune: "Asymmetric Induction to meso-Cyclohexane-1,2-diol Based on Diastereoselective Elimination." Tetrahedron Asymmetry. 4. 1767-1770 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Suemune: "Activation of Carbonyl Function by 1,2-Diol;Novel Asymmetric Spirocylization Based on Acid-Catalyzed Conjugate Addition." J.Chem.Soc.,Chem.Commun.1858-1859 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Nagumo: "Novel Ring Cleavage Based on Intermolecular Aldol Condensation." Tetrahedron. 49. 10501-10510 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Sakai: "Review:Application of Chiral Cyclic Diols to Asymmetric Synthesis." Tetrahedron:Asymmetry,. 4. 2109-2118 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Kato: "Preparation of Opitically Active Tricyclic 1,4-Dioxepin-5-one Derivatives and Its Application to Asymmetric Alkylation." Heterocycles. 37. 413-423 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Kato: "Asymmetric Alkylation Using Chiral Cyclic Diols to Prepare a Quaternary Carbon." Tetrahedron. 50. 3315-3326 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Kato: "Asymmetric Oxidation of β-Keto Esters Using Chiral Cyclic Diols." Tetrahedron Lett.35. 3103-3104 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Suemune: "Enantio-and Diastereo-selective Synthesis of Spirocyclic Compounds." J.Chem.Soc.,Perkin Trans.1. 3441-3447 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Suemune: "Highly Enantio-and Diastereoselective Synthesis of C_2-symmetric Cyclohexane-1,2,4,5-tetrol" Tetrahedron:Asymmetry. 6. 55-58 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Ogawa: "Synthetic Approach to 1,3-Polymethyl Function Based on Diastereoselective Conjugate Addition." Chem.Pharm.Bull.41. 1652-1654 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Kato: "New Type of Asymmetric Double Michael Reaction Induced by Chiral Acetal." Tetrahedron Lett.34. 4979-4980 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Suemune: "Asymmetric Induction to meso-Cyclohexane-1,2-diol Based ton Diastereoselective Elimination." Tetrahedron Asymmetry. 4. 1767-1770 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Suemune: "Activation of Carbonyl Function by 1,2-Diol ; Novel Asymmetric Spirocyclization Based on Acid-Catalyzed Conjugate Addition." J.Chem.Soc., Chem.Commun.1858-1859 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Nagumo: "Novel Ring Cleavage Based on Intermolecular Aldol Condensation." Tetrahedron. 49. 10501-10510 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Sakai: "Review : Application of Chiral Cyclic Diols to Asymmetric Synthesis." Tetrahedron : Asymmetry. 4. 2109-2118 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Kato: "Preparation of Optically Active Tricyclic 1,4-Dioxepin-5-one Derivatives and Its Application to Asymmetric Alkylation." Heterocycles. 37. 413-423 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Kato: "Asymmetric Alkylation Using Chiral Cyclic Diols to Prepare a Quaternary Carbon." Tetrahedron. 50. 3315-3326 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Kato: "Asymmetric Oxidation of beta-Keto Esters Using Chiral Cyclic Diols." Tetrahedron Lett.35. 3103-3104 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Suemune: "Enantio-and Diastereo-selective Synthesis of Spirocyclic Compounds." J.Chem.Soc., Perkin Trans.1. 3441-3447 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Suemune: "Highly Enantio- and Diastereoselective Synthesis of C_2-symmetric 3,5-Cyclohexadiene-1,2-diol and D_2-symmetric Cyclohexane-1,2,4,5-tetrol" Tetrahedron : Asymmetry. 6. 55-58 (1995)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1996-04-15  

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