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Scope and Limitations of Chiral B-[3,5-Bis(trifluoromethyl)phenyl]oxazaborolidine Catalyst for Use in the Mukaiyama Aldol Reaction
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Section: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.
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History
- Published In Issue December 29, 2000
- Received August 22, 2000
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