Akin to the dihydroxylation, the oxyamination involves the cycloaddition of the alkene to an imido Os(VIII) intermediate of the type OsO3(NR). Such species are generated by treatment of
osmium tetroxide with the sodium chloramines. Typical procedures combine
chloramine-T, alkene, an osmium catalyst, and a chiral ligand.[2] Related procedures use
benzyl carbamate (CbzNH2), sodium hydroxide,
tert-butyl hypochlorite to give CbzNCl(Na).[3]
R2NH + t-BuOCl → R2NCl + t-BuOH
Further reading
Early papers in the development of this methodology.