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Synlett 1990; 1990(4): 230-232
DOI: 10.1055/s-1990-21047
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An Anomalous Case of Diastereoselectivity in Diels-Alder Reactions Using Chiral Dienes: Is π Stacking Involved?

Joseph P. Lyssikatos* , Mark D. Bednarski
  • *Department of Chemistry, University of California, Berkeley, California 94720, USA
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Publication Date:
08 March 2002 (online)

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Two new chiral dienes, compounds 1 and 2, we synthesized and reacted with maleic anhydride at room temperature. When R is a phenyl group the diastereofacial selectivity is 10:1. Curiously when R is a cyclohexyl group this ratio decreases to 2:1.