Regio- and stereospecific cleavage of stannylepoxides with lithium phenylsulfide

Unsubstituted and alpha or beta C-substituted epoxystannanes react with lit hium phenylsulfide to give regio- and stereodefined alpha -phenylthio-beta -hydroxystannanes resulting from alpha -opening with inversion of configura tion. On the other hand, alpha- or beta -trans-silyl epoxystannanes afford stereospecific alpha- or beta -silylated vinylsulfides formed by nucleophil ic attack at the carbon which bears the tin group and subsequent syn-elimin ation of HOSnBu3. Both types of products are interesting synthons in organi c chemistry. (C) 2001 Elsevier Science Ltd. All rights reserved.