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Synlett 2004(8): 1399-1403
DOI: 10.1055/s-2004-829091
DOI: 10.1055/s-2004-829091
LETTER
© Georg Thieme Verlag Stuttgart · New York
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
Further Information
Received
17 May 2004
Publication Date:
22 June 2004 (online)
Publication History
Publication Date:
22 June 2004 (online)
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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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