Mechanistic Insights into the Factors Determining Exo−Endo Selectivity in the Lewis Acid-Catalyzed Diels−Alder Reaction of 1,3-Dienes with 2-Cycloalkenones
Organic Letters2000Vol. 2(13), pp. 1927–1929
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Abstract
We adduce evidence that the asynchronous, Lewis acid-catalyzed Diels-Alder reaction of 2-cycloalkenones with nonsimple alpha,beta-enones can proceed via transition states in which the 1,3-diene subunit is skewed, i.e., nonplanar, with profound effects on the ratio of exo and endo addition products.
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