Chemistry of oxaziridines. 17. N-(Phenylsulfonyl)(3, 3-dichlorocamphoryl) oxaziridine: a highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides

…, RT Reddy, W Han, PJ Carroll

Index: Davis, Franklin A.; Thimma Reddy; Han, Wei; Carroll, Patrick J. Journal of the American Chemical Society, 1992 , vol. 114, # 4 p. 1428 - 1437

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Citation Number: 150

Abstract

Abstract: The synthesis, structure, and enantioselective oxidations of a new chiral N- sulfonyloxaziridine 12c [3, 3-dichloro-1, 7, 7-trimethyl-2'-(phenylsulfonyl) spiro [bicyclo [2.2. 1] heptane-2, 3'-oxaziridine]] are reported. This oxidant, which exhibits remarkably high and predictable ee's for the enantioselective oxidation of prochiral sulfides to sulfoxides, is prepared in three steps from (+)-or (-)-camphor in 50% overall yield. Steric effects are ...