TDAE Strategy for the Synthesis of 2,3-Diaryl N-Tosylaziridines

Abstract

We report herein an original and rapid synthesis of 2,3-diaryl N-tosylaziridines by TDAE strategy starting from ortho- or para-nitro(dichloromethyl)benzene derivatives and N-tosylimines. A mixture of cis/trans isomers was isolated from 1-(dichloromethyl)-4-nitrobenzene, whereas only trans-aziridines were obtained from ortho-nitro derivatives.

Keywords

• TDAE
• N-tosylimines
• aziridines
• diastereoselectivity