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Highly Enantioselective Cyanosilylation of Aldehydes Catalyzed by a Chiral Oxazaborolidinium Ion

Do Hyun Ryu and E. J. Corey*

*Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts, 02138, Email: coreychemistry.harvard.edu

D. H. Ryu, E. J. Corey, J. Am. Chem. Soc., 2004, 126, 8106-8107.

DOI: 10.1021/ja0475959


Abstract

Chiral oxazaborolidinium salts are excellent catalysts for a highly enantioselective cyanosilylation of various aldehydes using trimethylsilyl cyanide and triphenylphosphine oxide as the source of a new reactive cyanide donor. A mechanistic model allows the prediction of the absolute configuration of cyanohydrin products.

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Key Words

Cyanohydrins


ID: J48-Y2004-1540