高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 21.

• Plenary, Keynote and Invited Lectures • 上一篇    下一篇

Attractive π-Interaction as an Efficient Control Element for Acyclic Stereocontrol

Teck-Peng Loh   

  1. Department of Chemistry, National University of Singapore, 10 Kent Ridge Crescent, Singapore 119260
  • 出版日期:1998-12-31 发布日期:1998-12-31

Attractive π-Interaction as an Efficient Control Element for Acyclic Stereocontrol

Teck-Peng Loh   

  1. Department of Chemistry, National University of Singapore, 10 Kent Ridge Crescent, Singapore 119260
  • Online:1998-12-31 Published:1998-12-31

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摘要： During the course of our synthetic studies of a natural product, an indium-mediated allylation reaction in aqueous media has been developed as the key step for the assembly of the advanced intermediate 2 (Scheme 1) in our strategy. The reaction proceeds with very high diastereoselectivity (>99% de), a result rare for acyclic molecules in the absence of obvious steric interaction or intramolecular chelation.1 The interlocking physical, chemical and computational studies undertaken supported a π-stacking effect between the phenyl ring with the ketone.

Abstract: During the course of our synthetic studies of a natural product, an indium-mediated allylation reaction in aqueous media has been developed as the key step for the assembly of the advanced intermediate 2 (Scheme 1) in our strategy. The reaction proceeds with very high diastereoselectivity (>99% de), a result rare for acyclic molecules in the absence of obvious steric interaction or intramolecular chelation.1 The interlocking physical, chemical and computational studies undertaken supported a π-stacking effect between the phenyl ring with the ketone.

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