Stereoselective Monoamine Oxidase-Catalyzed Oxidative Aza-Friedel-Crafts Reactions of meso-Pyrrolidines in Aqueous Buffer.

We disclose the highly diastereoselective combination of monoamine oxidase-catalyzed oxidation of meso-pyrrolidines and aza-Friedel–Crafts reactions in aqueous buffer to give valuable enantioenriched 2-substituted pyrrolidines in a formal double CH activation process. A range of secondary as well as tertiary amines were shown to be suitable substrates for the biocatalytic oxidation and subsequent addition of a variety of C-nucleophiles.