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Regioselective and Asymmetric Diels-Alder Reaction of 1- and 2-Substituted Cyclopentadienes Catalyzed by a Brønsted Acid Activated Chiral Oxazaborolidine

Joshua N. Payette and Hisashi Yamamoto*

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

J. N. Payette, H. Yamamoto, J. Am. Chem. Soc., 2007, 129, 9536-9537.

DOI: 10.1021/ja0735958 (free Supporting Information)


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Abstract

A cationic oxazaborolidine salt affords Diels-Alder adducts of ethyl acrylate and substituted cyclopentadienes, derived from the corresponding mixture of regioisomers, as single isomers in excellent yields and enantioselectivities.

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Key Words

Diels-Alder Reaction


ID: J48-Y2007-2590