Journal
SYNTHETIC COMMUNICATIONS
Volume 34, Issue 7, Pages 1337-1347Publisher
MARCEL DEKKER INC
DOI: 10.1081/SCC-120030324
Keywords
aziridination; N-arylsulfonyl aziridine; p-toluenesulfonamide; alkenes
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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.
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