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.
Bibliographical noteFunding Information:
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.
Copyright 2008 Elsevier B.V., All rights reserved.
- N-Arylsulfonyl aziridine