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We report a novel copper(II)-catalyzed aminohydroxylation in which both heteroatoms of an N -sulfonyl oxaziridine are added across an alkene in a regioselective fashion. A variety of styrenes and electron-rich alkenes can be aminohydroxylated using this protocol. Preliminary investigations indicate that this new process is a rare non-oxenoid reaction of N -sulfonyl oxaziridines, involving a stepwise, polar mechanism rather than a concerted process.
Michaelis et al. (Tue,) studied this question.