高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 160.

• Organic Synthesis Chemistry • 上一篇    下一篇

Facile One-pot Transformation of 2,3-Epoxy Alcohols into Allylic Alcohols

Zuosheng LIU, Jiong LAN, Yulin LI   

  1. National Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000
  • 出版日期:1998-12-31 发布日期:1998-12-31
  • 基金资助:
    This work was financially supported by the National Nature Science Foundation of China (Grant No. 29672015)

Facile One-pot Transformation of 2,3-Epoxy Alcohols into Allylic Alcohols

Zuosheng LIU, Jiong LAN, Yulin LI   

  1. National Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000
  • Online:1998-12-31 Published:1998-12-31
  • Supported by:
    This work was financially supported by the National Nature Science Foundation of China (Grant No. 29672015)

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摘要： Optically-active allylic alcohols have been frequently used as chiral building blocks for the preparation of optically pure compounds.1 There are at present various methods for the synthesis of optically active allylic alcohols including the kinetic resolution racemic allylic alcohols,2 reductive rearrangement of 2,3-epoxy alcohol by metal, halide and telluium-based chemistry.3 To our knowledge, One-pot Transformation of 2,3-epoxy alcohols into allylic alcohols, especially via epoxy iodides,is limited to Dorta's method3 using a Ph3P,iodine, imidazole,2,6-lutidine and water system. The original Dorta's method can be successfully applied to the formation of tertiary allylic alcohols, but give unsatisfactory results in formation of secondary allylic alcohols.

Abstract: Optically-active allylic alcohols have been frequently used as chiral building blocks for the preparation of optically pure compounds.1 There are at present various methods for the synthesis of optically active allylic alcohols including the kinetic resolution racemic allylic alcohols,2 reductive rearrangement of 2,3-epoxy alcohol by metal, halide and telluium-based chemistry.3 To our knowledge, One-pot Transformation of 2,3-epoxy alcohols into allylic alcohols, especially via epoxy iodides,is limited to Dorta's method3 using a Ph3P,iodine, imidazole,2,6-lutidine and water system. The original Dorta's method can be successfully applied to the formation of tertiary allylic alcohols, but give unsatisfactory results in formation of secondary allylic alcohols.

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