Scope and Limitations of Chiral B-[3,5-Bis(trifluoromethyl)phenyl]oxazaborilidine Catalyst for Use in the Mukaiyama Aldol Reaction

Kazuaki Ishihara, Shoichi Kondo, Hisashi Yamamoto*

*Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, Email: yamamotouchicago.edu

K. Ishihara, S. Kondo, H. Yamamoto, J. Org. Chem., 2000, 65, 9125-9128.

DOI: 10.1021/jo001271v

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Abstract

A new chiral oxazaborolidine 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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proposed extended-transition state assembly

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BINAP/AgOTf/KF/18-Crown-6 as New Bifunctional Catalysts for Asymmetric Sakurai-Hosomi Allylation and Mukaiyama Aldol Reaction

M. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem., 2003, 68, 5593-5601.

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Key Words

Mukaiyama Aldol Addition, chiral oxazaborolidines, silyl enol ethers

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ID: J42-Y2000-080