Exploration of One-Pot, Tandem Sulfamoylation and aza-Michael Cyclization Reactions for the Syntheses of Oxathiazinane Dioxide Heterocycles

We show the first examples of one-pot tandem sulfamoylation/aza-Michael reactions for the preparation of oxathiazinane dioxide heterocycles from linear alkenyl alcohol precursors. Our optimized protocols are tolerant of a variety of functional groups and provide products that are amenable for further transformations. The reactions scale well, and no special precautions are required to exclude air or ambient moisture.