Oxaziridines, by virtue of their weak N-O bonds and strained three-membered heterocyclic rings, possess unusual reactivity and have been exploited for their heteroatom-transfer reactions. Highly regio- and chemo-selective intramolecular C-H oxidation has been achieved via copper-catalyzed transformation of oxaziridines to allylic alcohols. The C-H oxidation proceeds with moderate to good yields with a variety of substrates including one example with an unactivated tertiary C-H bond. Initial mechanistic insight has been deduced using a radical-trapping experiment with TEMPO.

Copper-catalyzed oxaziridine-mediated intramolecular C-H bond oxidation

244th National Meeting (2012)

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