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Synthesis of α-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines

Franklin A. Davis, Lal C. Vishwakarma, Joanne G. Billmers and John Finn

*Department of Chemistry, Drexel University Philadelphia, Pennsylvania 19104

F. A. Davis, L. C. Vishwakarma, J. G. Billmers, J. Finn, J. Org. Chem., 1984, 49, 3241-3243.

DOI: 10.1021/jo00191a048


Direct oxidation of ketone and ester enolates with a 2-sulfonyloxazaridine provides α-hydroxy carbonyl or carboxyl compounds in high yield with excellent stereochemistry.

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Key Words

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

ID: J42-Y1984