Regio- and stereospecific cleavage of stannylepoxides with lithium phenylsulfide

Unsubstituted and α or β C-substituted epoxystannanes react with lithium phenylsulfide to give regio- and stereodefined α-phenylthio-β-hydroxystannanes resulting from α-opening with inversion of configuration. On the other hand, α- or β-trans-silyl epoxystannanes afford stereospecific α- or β-silylated vinylsulfides formed by nucleophilic attack at the carbon which bears the tin group and subsequent syn-elimination of HOSnBu3. Both types of products are interesting synthons in organic chemistry.