A synthesis of allylsilanes in which the silyl group is at the more-substituted end of the allyl group

Abstract

The allylsilanes (8), (11), (18)–(20), and (26), have been made by a three-step sequence from αβ-unsaturated esters. The steps are conjugate addition of the phenyldimethylsilyl group, lithium aluminium hydride reduction, and selenium-mediated dehydration. The route is versatile and leads regiospecifically to allylsilanes, in which the silyl group is at the more-substituted end of the allyl group.