The N-heterocyclic Carbene (NHC)-mediated unconventional activation of enals often leads to homoenolate equivalents as the reactive intermediates. Here we report selective catalytic generation of enolate and acyl anion equivalents from simple enals that undergo highly enantioselective intermolecular Diels-Alder and Stetter reactions respectively with alkylidene diketones. The enal �-substituents play an important role in directing the two reaction pathways: �-aryl enal favors the Diels-Alder reactions, while �-alkyl enals exclusively undergo Stetter reactions. No products resulted from the typical homoenolate equivalent intermediates were observed under a range of conditions.

Enal β-substituents-directed enatioselective Diels-Alder reactions and Stetter reactions of enals and modified chalcones catalyzed by N-heterocyclic carbenes

243rd National Meeting (2012)

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