OXYGEN ATOM TRANSFER FROM A CHIRAL N-ALKYL OXAZIRIDINE PROMOTED BY ACID. THE ASYMMETRIC OXIDATION OF SULFIDES TO SULFOXIDES

Abstract Chiral N-alkyl oxaziridines may be used as reagents for the asymmetric oxidation of sulfides in an acid-promoted reaction leading exclusively to the corresponding sulfoxides A planar transition state geometry seems consistent with the observed stereochemistry which should result from the steric interactions in the transition state. The influence of the solvent and the acid strength on the oxygen transfer reaction are discussed.