Catalytic asymmetric cyanosilylation of ketones by a chiral amino acid salt

In this Communication, we describe the first highly enantioselective cyanosilylation of ketones catalyzed by simple chiral amino acid salt. A broad range of aromatic, α,β-unsaturated, heterocyclic ketones catalyzed by L-phenylglycine sodium salt gave the corresponding trimethylsilyl ethers of cyanohydrins in 75-96% yields with 86-97% enantioselectivities. A catalytic cycle based on experimental phenomena and studies has been proposed to explain the origin of this activation. The reaction employed commercially available and fully recyclable catalysts and involves a simple experimental procedure. Copyright © 2005 American Chemical Society.