Asymmetric Reaction of<i>p</i>-Quinone Diimide: Organocatalyzed Michael Addition of α-Cyanoacetates

Abstract

Hitherto unknown catalytic enantioselective transformation of p-quinone diimides is achieved using chiral bifunctional organic molecules. Bifunctional thiourea compounds catalyze the Michael addition of cyanoacetates with excellent yields and enantioselectivities. The initially formed Michael adducts undergo cyclization to yield functionally rich, fused cyclic imidines bearing a quaternary benzylic chiral center. Density functional theory calculations of the competing transition states (TSs) were carried out to explain the observed stereochemical outcome.