Enantioselective and Structure-Selective Diels−Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules
- 25 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (15) , 4800-4802
- https://doi.org/10.1021/ja049323b
Abstract
The chiral oxazaborolidinium cation 1 promotes Diels−Alder reactions between 2-triisopropylsilyloxy-1,3-butadiene and a number of unsymmetrical 1,4-benzoquinones in a highly enantioselective and structurally selective manner. The basis for the enantioselectivity is explained rationally in terms of a preferred type of transition-state assembly. Selection rules have been developed that allow the prediction of the principal reaction product of Diels−Alder reaction between unsymmetrical diene and quinone components.Keywords
This publication has 1 reference indexed in Scilit:
- Asymmetric Diels−Alder Reactions Catalyzed by a Triflic Acid Activated Chiral OxazaborolidineJournal of the American Chemical Society, 2002