Enantiomerically pure 2-alkyl and 2,3-dialkylaziridines from 2- sulfinylimines

Article abstract of DOI:10.1016/S0040-4039(98)02168-6

A new entry to optically pure azifidines from N-p-methoxyphenyl derivatives of 2-p-tolylsulfinylketimines is reported. The highly stereoselective reduction of the imines with DIBAL-H/ZnX₂ yielded the corresponding sulfinyl amines, which can be transformed info the N-Cbz derivatives through a two-step sequence involving reaction with BnO₂CCl and subsequent oxidation with CAN. These compounds were easily transformed into optically pure aziridines by reduction of the sulfinyl group, further methylation at sulfur, and final cyclization with base.