Abstract
Summary: The Cu(1)- or Cu(I1)-catalyzed aziridination of both electron-rich and electron-deficient olefins em- ploying (N-do-toluenesulfonyl)imino)phenyliodinane, PhI=NTs, as the nitrene precursor, affords N-tosyl- aziridines in yields ranging between 55%-95%. In a seminal 1967 publication, Kwart and Kahn' re- ported the copper-bronze-catalyzed aziridination and al- lylic insertion reactions of benzenesulfonylazide with cy- clohexene. Subsequently, Mansuy disclosed that aziridi- nation of a number of olefins can be achieved with (N- (p-toluenesulfony1)imino)phenyliodinane (PhI=NTs)2 using Fe(II1)- and Mn(II1)-porphyrins as catlysts.3 Other evidence for catalytic imido group transfer has appeared in the literat~re;~ however, the number of olefinic sub- strates, nitrene precursors, and catalysts that have been evaluated in these studies has been limited. In view of the demonstrated utility of suitably functionalized aziridines in organic synthesis: it is noteworthy that the
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