Asymmetric Synthesis of γ-Nitroesters by an Organocatalytic One-Pot Strategy

An enantioselective synthesis of gamma-nitroesters by a one-pot asymmetric Michael addition/oxidative esterification of alpha,beta-unsaturated aldehydes is presented. The procedure is based on merging the enantioselective organocatalytic nitroalkane addition with an N-bromosuccinimide-based oxidation. The gamma-nitroesters are obtained in good yields and enantioselectivities, and the method provides an attractive entry to optically active gamma-aminoesters, 2-piperidones, and 2-pyrrolidones.