Organocatalytic Disulfonylation of Mono- and 1,2-Disubstituted Epoxides by Using Pyridine N-Oxide

Abstract A convenient, stereoselective organocatalytic disulfonylation of epoxides was developed. This reaction uses various sulfonic anhydrides, such as methanesulfonic anhydride or p-toluenesulfonic anhydride, and is catalyzed by pyridine N-oxide derivatives. Washing the sulfonic anhydrides with Et2O was key to the success of the reaction. Several disulfonylated vicinal diols were obtained in high yields. The reaction was also applied to 1,2-disubstituted epoxides to provide anti-disulfonylated vicinal diols in high yield.