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

…, AC Sheppard, BC Chen, MS Haque

Index: Davis, Franklin A.; Sheppard, Aurelia C.; Chen, Bang-Chi; Haque, M. Serajul Journal of the American Chemical Society, 1990 , vol. 112, # 18 p. 6679 - 6690

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Citation Number: 144

Abstract

Abstract: The reagentantrolled asymmetric oxidation of tri-and tetrasubstituted ketone enolate anions 4 and 8 by enantiomerically pure (camphorylsulfony1) oxaziridine 2 has been investigated. The stereoselectivities for oxidation of trisubstituted enolates 4a-d are good to excellent, 60-95% ee, while those for tetrasubstituted enolates 4e and 8 are lower: Le., 21-30% ee. Isolated chemical yields for both types of enolate anions are good to ...

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