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2-(Phenylsulfonyl)-3-phenyloxaziridine, Davis Reagent

2-(Phenylsulfonyl)-3-phenyloxaziridine is an especially useful reagent for the α-hydroxylation of ketones and esters, known as Davis Oxidation.

Name Reactions

Davis Oxidation

Recent Literature

Direct oxidation of ketone and ester enolates with a 2-sulfonyloxazaridine provides α-hydroxy carbonyl or carboxyl compounds in high yield with excellent stereochemistry.
F. A. Davis, L. C. Vishwakarma, J. G. Billmers, J. Finn, J. Org. Chem., 1984, 49, 3241-3243.

2-(Phenylsulfonyl)-3-phenyloxaziridine, commonly known as the Davis reagent, enables a generation of sulfinate anions by oxidation of the corresponding thiolates. Subsequent S-alkylation of the sulfinates under phase-transfer catalysis affords sulfones in very good isolated yields.
F. Sandrinelli, S. Perrio, P. Beslin, Org. Lett., 1999, 1, 1107-1109.