Novel stereoselective synthesis of all four diastereomers of 3a-methyl-pyrrolo[3,4-c]piperidine from glycine ethyl ester

Abstract Asymmetric synthesis of all four diastereomers of 3a-methyl-pyrrolo[3,4-c]piperidine is described herein. The key steps in this synthesis are the highly diastereoselective hydrogenation of an alkenyl nitrile through a hydroxyl-directed or sterically controlled hydrogenation, and the resolution of enantiomers using a chiral auxiliary.