Highly Enantioselective Cyanosilylation of Aldehydes Catalyzed by a Chiral Oxazaborolidinium Ion
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- 9 June 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (26) , 8106-8107
- https://doi.org/10.1021/ja0475959
Abstract
The chiral oxazaborolidinium salts 1 and 2 are excellent catalysts for the enantioselective cyanosilylation of a wide variety of aldehydes (see Table 1) using trimethylsilyl (TMS) cyanide and triphenylphosphine oxide as the source of a new reactive cyanide donor. This donor appears to be the isocyanophosphorane Ph3P(OTMS)(NC:) (4). The novel process described herein has several advantages: predictability of absolute configuration of cyanohydrin products from a mechanistic model (3), high yields and very good enantiomeric purity of products (≥90%), and, finally, easy and efficient recovery of the catalytic ligand.Keywords
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