Enantioselective Biocatalytic Oxidative Desymmetrization of Substituted Pyrrolidines

Abstract

Made up out of air: The highly enantioselective oxidation of 3,4-substituted meso-pyrrolidines to Δ1-pyrrolines is reported. The reaction is catalyzed by monoamine oxidase from Aspergillus niger (MAO-N D5) and utilizes molecular oxygen from air as the stoichiometric oxidant. The corresponding Δ1-pyrrolines serve as useful building blocks for the synthesis of L-proline analogues and α-amino nitriles of high enantiomeric purity.