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Published June 29, 2000 | public
Journal Article

Mechanistic Insights into the Factors Determining Exo−EndoSelectivity in the Lewis Acid-Catalyzed Diels−Alder Reaction of 1,3-Dienes with 2-Cycloalkenones


We adduce evidence that the asynchronous, Lewis acid-catalyzed Diels−Alder reaction of 2-cycloalkenones with nonsimple α,β-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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© 2000 American Chemical Society. Received 1 May 2000. Published online 27 May 2000. Published in print 1 June 2000. This research was assisted financially by a grant from the National Institutes of Health.

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