Sharpless oxyamination
# Sharpless oxyamination

The Sharpless oxyamination (often known as Sharpless aminohydroxylation) is the chemical reaction that converts an alkene to a vicinal amino alcohol. The reaction is related to the Sharpless dihydroxylation, which converts alkenes to vicinal diols. Vicinal amino-alcohols are important products in organic synthesis and recurring pharmacophores in drug discovery.

## Mechanism

Akin to the dihydroxylation, the oxyamination involves the cycloaddition of the alkene to an imido Os(VIII) intermediate of the type $OsO_3(NR).$ 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. Related procedures use benzyl carbamate $(CbzNH_2),$ sodium hydroxide, tert-butyl hypochlorite to give CbzNCl(Na).

    $R_2NH$ + t-BuOCl → $R_2NCl$ + t-BuOH
