L-Proline catalyzed highly efficient synthesis of Z-5-alkylidene cyclic sulfamidate imines: An easy access to 5-alkyl-substituted cyclic sulfamidate imines

Abstract

A very simple, mild and robust method for the synthesis of exclusively Z-trisubstituted 5-alkyliden cyclic sulfamidate imines via a condensation reaction of 4-aryl-5H-1,2,3-oxathiazole-2,2-dioxides with aldehydes using l-proline as an organocatalyst at room temperature is reported for the first time. In addition, the synthesis of 5-alkyl substituted cyclic sulfamidate imines, trans-β-amino-α-azido/triazole and 2-hydroxy-4-triazole-5- phenylpyrrolidine derivatives have been developed through this methodology. © The Royal Society of Chemistry 2013.