Synthesis of Vinyl Silanes from Vinyl Silane Phosphates

Article abstract of DOI:10.1021/jo00265a005

To develop a new synthesis of vinyl silanes, a representative set of vinyl silane phosphates (VSP's) has been treated with several organocuprate reagents.With acyclic VSP's, phosphate substitution proceeds in generally good yields, giving a single stereoisomer of the vinyl silane with retention of the VSP stereochemistry.In the cyclic systems examined, yields are generally somewhat lower under the same reactions conditions.However, this new sequence offers a regiochemistry complementary to other syntheses of cyclic vinyl silanes, and an approach to higly substituted vinyl silanes applicable to both cyclic and acyclic systems.