Asymmetric bisboranes as bidentate catalysts for carbonyl substrates.

Org Lett

Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.

Published: February 2009

A new class of C(2) symmetric bisoxazaborolidinone compounds is described which exhibits bidentate binding to carbonyl substrates. Using the Diels-Alder reaction as a model system, the catalytic activity of these bis-Lewis acids is probed. Reaction rates and selectivities are observed that are higher than the corresponding mono-Lewis acids. This novel system offers a potentially powerful new approach to asymmetric Lewis acid catalysis.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2662717PMC
http://dx.doi.org/10.1021/ol802793kDOI Listing

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