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

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.