Synthesis of Functionalized Sulfonamides via 1,3-Dipolar Cycloaddition of Pentafluorophenyl Vinylsulfonate

Abstract

[reaction: see text] An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.