Advances in the Chemistry of Oxaziridines

Oxaziridines constitute a subset of a class of versatile oxidants whose characteristic feature is the presence of two electronegative heteroatoms within a strained three-membered ring (Figure (Figure1).1). Other small organic heterocycles in this class include diaziridines1 and dioxiranes,2 which have been developed as reagents for a variety of oxidative transformations. η2-Peroxo and η2-hydroperoxy complexes of various transition metals are also members of this class,3 and these structures are the active oxidizing species in a broad range of synthetically useful oxidative transformations, including the Sharpless asymmetric epoxidation,4 VO(acac)2-catalyzed epoxidations,5 and MeReO3-catalyzed hydroxylation of unactivated alkanes.6 Peroxometal complexes are relevant in biological systems as well; dinuclear μ-η2:η2-peroxodicopper(II) complexes found within the active sites of metalloenzymes such as hemocyanin and tyrosinase have been extensively studied for their role in oxygen metabolism.7 Figure 1 Representative oxidizing heterocycles with two electrophilic heteroatoms within a three-membered ring.