title: 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.
authors.affiliation: Centre for Biomolecular Design and Drug Development, The Chemistry Laboratory, University of Sussex, Falmer, Brighton BN1 9QJ, UK. s.caddick@sussex.ac.uk
authors.forename: Stephen
authors.initials: S
authors.lastname: Caddick
authors.forename: Hannah D
authors.initials: HD
authors.lastname: Bush
mesh_terms: D013449:Sulfonamides / Q000138:chemical synthesis*; D013451:Sulfonic Acids / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*; D005464:Fluorobenzenes; D005466:Fluorocarbons
chemical_list: D013449:Sulfonamides; D013451:Sulfonic Acids; D014753:Vinyl Compounds; C478988:pentafluorophenyl vinylsulfonate; D005464:Fluorobenzenes; D005466:Fluorocarbons