In Situ Enamine Activation in Aqueous Salt Solutions: Highly Efficient Asymmetric Organocatalytic Diels–Alder Reaction of Cyclohexenones with Nitroolefins

Abstract

Deep-sea Diels-Alder: The asymmetric organocatalytic Diels-Alder reaction of cyclohexenones with aromatic nitroolefins can be carried out in seawater and brine. The reaction proceeds by an in situ enamine activation involving a one-step concerted addition pathway (see scheme).