Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl)oxaziridine

Franklin A. Davis, Aurelia C. Sheppard, Bang Chi Chen and M. Serajul Haque

*Department of Chemistry, Drexel University Philadelphia, Pennsylvania 19104

F. A. Davis, A. C. Sheppard, B. C. Chen, M. S. Haque, J. Am. Chem. Soc., 1990, 112, 6679-6690.

DOI: 10.1021/ja00174a035

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Abstract

An enantiomerically pure (camphorsulfonyl)oxaziridine enables a reagent-controlled asymmetric oxidation of tri- and tetrasubstituted ketone enolate anions. Whereas the stereoselectivities for trisubstituted enolates are very good, those for tetrasubstituted enolates are lower.

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Key Words

Davis Oxidation, α-hydroxy ketones

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ID: J48-Y1990