Scope and Limitations of Chiral B-[3,5-Bis(trifluoromethyl)phenyl]oxazaborolidine Catalyst for Use in the Mukaiyama Aldol Reaction
- 1 December 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (26) , 9125-9128
- https://doi.org/10.1021/jo001271v
Abstract
A new chiral oxazaborolidine catalyst was prepared in situ from 3, 5-bis(trifluoromethyl)phenylboron dichloride and N-(p-toluenesulfonyl)-(S)-tryptophan. This catalyst is much more active than Corey's original catalyst for the Mukaiyama aldol reaction of aldehydes with silyl enol ethers. The observed syn selectivities and re-face attack of silyl enol ethers on carbonyl carbon of aldehydes imply that the extended-transition state model is applicable.Keywords
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