Catalytic Asymmetric Cyanosilylation of Ketones by a Chiral Amino Acid Salt
Journal of the American Chemical Society2005Vol. 127(35), pp. 12224–12225
Citations Over TimeTop 10% of 2005 papers
Abstract
In this Communication, we describe the first highly enantioselective cyanosilylation of ketones catalyzed by simple chiral amino acid salt. A broad range of aromatic, alpha,beta-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.
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