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Studies on A Novel Asymmetric Cycloaddition Using Optically Active <alpha> , <beta> -Unsaturated Sulfoxides

Research Project

Project/Area Number 59570888
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionToyama Medical & Pharmaceutical University

Principal Investigator

KOIZUMI Toru  Professor, 薬学部, 教授 (40012611)

Co-Investigator(Kenkyū-buntansha) TAKAYAMA Hiromitsu  Assistant, 薬学部, 助手 (90171561)
ARAI Yoshitsugu  Assistant, 薬学部, 助手 (10115157)
TAKEUCHI Yoshio  Associate Professor, 薬学部, 助教授 (20111750)
Project Period (FY) 1984 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1986: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1985: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1984: ¥1,100,000 (Direct Cost: ¥1,100,000)
Keywords<alpha> , <beta> -Unsaturated Sulfoxides / Asymmetric Diels-Alder Reaction / Asymmetric Cycloaddition / 高ジアステレオ選択性
Research Abstract

Asymmetric Diels-Alder reaction using substituted arylsulfinylethenes (vinyl sulfoxides) has been studied. The high diastereoselectivity was interpreted in terms of the favored direction of the diene approach from the side of the sulfur lone pair in energetically favored s-cis or s-trans conformers and the conformational preferences in vinyl sulfoxides are rationalized on the basis of dipole-dipole and/or steric interactions between S-O and the substituents at <alpha> or <beta> position.
On the otherhand, the use of 2-pyridylsulfinyl group in place of p-tolyl-sulfinyl group enhanced the reactivity considerably and the high diastereoselectivity was also maintained by the cycloaddition with furan to give 7-oxabicyclo [2.2.1]hept-5-ene-2-carboxylic acid derivatives. The application of the asymmetric Diels-Alder reaction to the chiral synthesis of some biologically active natural products was achieved.

Report

(1 results)
  • 1986 Final Research Report Summary
  • Research Products

    (11 results)

All Other

All Publications (11 results)

  • [Publications] Arai Yoshitsugu: Tetrahedron Letters. 26. 6205-6208 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Arai Yoshitsugu: Synthetic Communications. 16. 233-244 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takayama Hiromitsu: Heterocycles. 24. 2137-2140 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takayama Hiromitsu: J.Chemical Society,Chemical Communications. 771-772 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takayama Hiromitsu: Tetrahedron Letters. 27. 5509-5512 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Arai Yoshitsugu: Chemistry Letters. 1225-1228 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Arai Yoshitsugu, Shuichi Kuwayama, Yoshio Takeuchi, and Toru Koizumi: "A Novel Chiral Dienophile Which Exhibits High Reactivity and Diastereoselectivity." Tetrahedron Letters. 26. 6205-6208 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Arai Yoshitsugu, Shuichi Kuwayama, Yoshio Takeuchi, and Toru Koizumi: "The First Synthesis of (+)-(S,S)-1,1-Bis(p-Tolylsulfinyl)ethene, A Latent Chiral Ketene Equivalent in Diels-Alder Reaction." Synthetic Communication. 16. 233-244 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Hiromitsu Takayama, Kazuya Hayashi, Yoshio Takeuchi, and Toru Koizumi: "Diels-Alder Reaction of 3-(2-Pyridylsulfinyl)acrylates.--The Enhancement of the Reactivity and the Diastereoselectivity by the Introduction of Electron-withdrawing Substituents on the Pyridine Ring." Heterocycles. 24. 2137-2140 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takayama Hiromitsu, Akira Iyobe, Toru Koizumi: "The First Efficient Asymmetric Synthesis of 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate Derivatives." J. Chemical Society, Chemical Communications. 771-772 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takayama Hiromitsu, Kazuya Hayashi, and Toru Koizumi: "Enantioselective Total Synthesis of Glyoxalase I Inhibitor Using Asymmetric Diels-Alder Reaction of A New Chiral Dienophile, (S)S-3-(3-Trifluoromethylpyrid-2-ylsulfinyl)acrylate." Tetrahedron Letters.27. 5509-5512 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary

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Published: 1987-03-31   Modified: 2016-04-21  

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