Asymmetric Intermolecular Stetter Reactions of Aromatic Heterocyclic Aldehydes­ with Arylidenemalonates

Abstract

The asymmetric Michael addition of aromatic heterocyclic aldehydes to arylidenemalonates catalyzed by N-heterocyclic carbenes is described. The ketomalonates are obtained in 84-98% yields and moderate to good enantioselectivities (30-78% ee). The enantiomeric excesses could be improved to excellent levels of up to 99% ee after a single recrystallization.

Stetter reaction - N-heterocyclic carbene - organocatalysis - nucleophilic acylation - umpolung

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