Organic Chemistry Portal



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:

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

DOI: 10.1021/ja0475959


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.

see article for more examples

Key Words


ID: J48-Y2004-1540