Stereoselective synthesis of enamides by a Peterson reaction manifold.

Vinylsilanes are converted into enamides by a sequence comprising epoxidation, nucleophilic ring opening of the resulting epoxysilanes with NaN(3), and reduction of the azide, followed by a "one-pot" N-acylation/Peterson elimination process. This method is distinguished by its wide applicability and stereoselective course. [reaction: see text]