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
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.
