N-Alkoxyl Templates for Diastereoselective Pyrrolidine Synthesis.

Intramolecular cyclization of N-alkoxyl amines are studied for the stereoselective preparation of 2, 4-disubstituted pyrrolidine derivatives. Reduction of oximes under acidic conditions by NaBH(3)CN afforded the corresponding nucleophilic hydroxylamine derivatives, which subsequently cyclized via S(N)2' mechanism to give the desired N-alkoxyl pyrrolidines.