Abstract: Ring opening of (2S, 3R)-1, 2-epoxy-4-penten-3-ol with N-benzylhydroxylamine hydrochloride and NaOMe in methanol gives the amine oxide (9) as a single diastereoisomer in 72% yield. Catalytic hydrogenation furnishes the parent homochiral pyrrolidine (10) in quantitative yield. Key words: pyrrolidines, asymmetric synthesis, cyclisation, hydroxylamine, reverse-Cope