Synthesis of functionalized N-arylsulfonyl aziridines from α,β-unsaturated esters, amides, ketones, and nitriles using N,N-dichloroarylsulfonamides as nitrogen source

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 C-2. 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.