Abstract

A versatile procedure for the γ –vinylogous aldol reaction of the dioxinone–derived silyl enolether, via enolate activation with an appropriate neutral Lewis base, was formulated. High levels of diastereo– and enantioselectivity using chiral 2–methylsulfinyl benzaldehyde were obtained, pointing out the dual role of the methylsulfinyl group as incorporated chiral inductor and activator of the silyloxydiene in the stereoselective vinylogous aldol reaction.

Keywords: Vinylogous, sulfoxide, Lewis Bases, asymmetric–induction, silyloxydiene.