Sharpless oxyamination

The reaction is related to the Sharpless dihydroxylation, which converts alkenes to vicinal diols.

[1] Vicinal amino-alcohols are important products in organic synthesis and recurring pharmacophores in drug discovery.

Akin to the dihydroxylation, the oxyamination involves the cycloaddition of the alkene to an imido Os(VIII) intermediate of the type OsO3(NR).

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).