Enantioselective scandium-catalyzed vinylsilane additions: a new approach to the synthesis of enantiopure beta,gamma-unsaturated alpha-hydroxy acid derivatives.

The development of the Lewis acid-catalyzed alkenylation using trimethylvinylsilanes is described. Both aliphatic and aromatic vinylsilanes were effective nucleophiles at room temperature affording chiral allylic alcohol products in excellent enantioselectivities (97 --> 99% ee) and in moderate to good yields (45-99%). Complete retention of vinysilane geometry was observed where applicable.