Davis Oxidation

The use of 2-(phenylsulfonyl)-3-phenyloxaziridine (Davis reagent) or similar oxaziridine reagents enables an oxidation of enolates generated in situ from ketones or esters to provide α-hydroxylated compounds.

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Mechanism of the Davis Oxidation

The transfer of oxygen from N-sulfonyloxaziridines to nucleophiles happens in a S_N2 mechanism, in which the enolate anion as nucleophile attacks the oxaziridine oxygen atom to give a hemiaminal intermediate.