Toward the Development of a General Chiral Auxiliary 10: Enhancement of Diastereoselectivity in Diels-Alder Reactions of Imides Derived from a New Bicyclic Lactam Chiral Controller Molecule

Robert K. Boeckman; Lisa M. Reeder

doi:10.1055/s-2004-829091

LETTER

Toward the Development of a General Chiral Auxiliary 10: Enhancement of Diastereoselectivity in Diels-Alder Reactions of Imides Derived from a New Bicyclic Lactam Chiral Controller Molecule

Jr., Robert K. Boeckman*, Lisa M. Reeder
Department of Chemistry, University of Rochester, P.O. Box 270216 Hutchison Hall, Rochester, New York 14627-0216, USA
Fax: +1(585)7560210; e-Mail: rkb@rkbmac.chem.rochester.edu;

Abstract

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Abstract

Based upon X-ray structural information derived from a series of camphor-derived bicyclic lactam chiral controller molecules, a new auxiliary has been designed which affords superior diastereoselectivity (>95:5) in Diels-Alder reactions with common dienes but of opposite π-facial selectivity than previously observed with this class of chiral controller. A rationale for the selectivity based on subtle structural changes in the chiral controller is discussed.

Key words

asymmetric cycloaddition - Lewis acid promoted - chiral controller - bicyclic lactams - structure vs. selectivity

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References

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