Organic Chemistry Portal

Abstracts

Search:

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


see article for more reactions

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.

see article for more examples



Key Words

Diels-Alder Reaction


ID: J48-Y2007-2590