(+)-(3-Oxocamphorsulphonyl)oxaziridune as a highly stereoselective reagent for the oxidation of sulphides to chiral sulphoxides

Abstract

The synthesis of the title oxaziridine and its application to the enantio- or diastereo-selective oxidation of sulphides to sulphoxides is described. Enantiomeric excesses up to 66% are observed, showing the reagent to be superior to most other oxidizing systems. The exceedingly mild reaction conditions (aprotic, neutral) allow the preparation of several chiral α-sulphinyl aldehydes. The properties of these compounds are discussed.