Preparation of optically pure propargylic and allylic alcohols from 2-(trimethylsilyl)vinyl sulfoxides as a chiral ethynyl anion synthon: computational studies on elimination reaction of 2-(trimethylsilyl)vinyl sulfoxides.
The reaction of the alpha-carbanion derived from (trimethylsilyl)vinyl sulfoxides with aldehydes afforded a diastereomeric mixture of the products. Each diastereomer was subjected to specific elimination reactions to give optically pure propargylic, trimethylsilylated propargylic, and allylic alcohols. Acceleration of the sulfenic acid-elimination from the beta-silylvinyl sulfoxide was demonstrated by the ab initio calculation to be ascribed mainly to the beta-effect of the silyl group.
Nakamura
Shuichi
S
Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Kusuda
Shinya
S
Kawamura
Kiyoshi
K
Toru
Takeshi
T