Synthesis of Functionalized N‐Arylsulfonyl Aziridines from α,β‐Unsaturated Esters, Amides, Ketones, and Nitriles Using N,N‐Dichloroarylsulfonamides as Nitrogen Source

Abstract

A convenient and general aziridination process has been developed for the synthesis of functionalized N‐arylsulfonylaziridines bearing an alkoxycarbonyl, acyl, cyano, and carboxamide group at C₂. The two‐step sequence involves addition of N,N‐dichloroarylsulfonamide to the appropriate olefin in the presence of Cu(acac)₂, treatment of the resultant chlorosulfonamide with Na₂SO₃, followed by cyclization with NaOH to give the appropriate aziridine in good yields. The reaction is found to be an anti‐stereoselective.

Keywords:

• Aziridination
• N‐Arylsulfonyl aziridine
• p‐Toluenesulfonamide
• Alkenes

Acknowledgment

This work was supported by project funds from Council of Scientific and Industrial research (CSIR), New Delhi (Government of India organization). The financial support provided by CSIR, New Delhi to AS in the form of senior research fellowship is acknowledged.