Synthesis of enantiomerically pure aziridine-2-imides by cyclization of chiral 3'-benzyloxyamino imide enolates

摘要

Aziridine-2-iides are pre prepared both in high yield and high diastereoselectivity form chiral 3'- benzyloxyamino imides 2,3 and 8 by treatment with triethylamine in the presence of either TiCl_4 or AIMe_2Cl. 2 and 3 are easily obtaind by a diastereoselective conjugate addition of O- benzylhydroxylamine promoted by Leis acids to α,β-unsaturated imides 1. The synthesis of 3'- (benzyloxyamino)propanoyl 8 is performed by addition to the acryloyl compound 6 of N-BOC O-benzylhydroxylamine followed by deprotection.