Cyanosilylation of aldehydes catalyzed by N-heterocyclic carbenes

N-Heterocyclic carbenes produced in situ from salts of imidazolium. benzimidazolium, pyrido[1,2-c]imidazolium, imidazolinium, thiazolium, and triazolium catalyze the addition of trimethylsilylcyanide to aldehydes to yield cyanohydrin trimethylsilyl ethers. The use of C-2-symmetric imidazolidenyl carbene derived from (R,R)-1,3-bis[(1-naphthyl)ethyl]imidazolium chloride led to enantioselective cyanosilylation. (c) 2006 Elsevier Ltd. All rights reserved.