Epoxidation of alkenes is a common reaction because epoxides can be derivatized in a number of useful ways. Classically, laboratory epoxidation is carried out with mCPBA or other peracids. Oxaziridines have been found to be useful for the formation of highly acid sensitive epoxides. (−)-Chaetominine was synthesized via oxaziridine epoxidation as a late stage transformation as seen below.
Another transformation of high synthetic utility is asymmetric epoxidation. A number of asymmetric epoxidations exist: the Sharpless epoxidation, the Jacobsen-Katsuki epoxidation, and the Juliá-Colonna epoxidation. These methods require specific functionality in order to achieve selectivity. The Sharpless epoxidation is specific to allylic alcohols, the Jacobsen epoxidation requires cis-disubstituted aryl alkenes, and the Juliá epoxidation requires α-β unsaturated ketones. Chiral oxaziridines act stereospecifically on many unfunctionalized alkenes. It has even possible to effect stereospecific epoxidation catalytically in the oxaziridine chiral unit. Further investigation into these reactions may be required before levels of enantiometic excess become practical for large scale synthesis. Lusinichi et al. have investigated asymmetric epoxidation with a chiral oxaziridinium salt using oxone as the stoichiometric oxidant seen below.