AbstractThe preparation of a series of chiral 3‐methyl‐3‐substituted‐pyrrolidines/pyrrolidinones starting from (R)‐4‐(methoxycarbonyl)‐1‐(1R‐phenethyl)‐2‐pyrrolidinone (1) is described. The chiral α‐methylbenzyl functionality serves not only as a nitrogen protecting group for the pyrrolidine nitrogen, but also as a chiral auxillary. The synthesis of the 4‐position enantiomers was accomplished by converting the ester of 1 to the ketone, protecting the ketone as the benzyloxime and separation by chromatography. These key intermediates were converted to the (R) and (S)‐3‐methyl‐3‐aminomethylpyrrolidines by removal of the benzyl group followed by oxidation. The 3‐methyl‐3‐(1‐aminoethyl)pyrrolidines were obtainedviaa two step reduction of the corresponding oximes. The stereochemical assignment