Synthesis of functionalized sulfonamides via 1,3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate.
[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.
Caddick
Stephen
S
Centre for Biomolecular Design and Drug Development, The Chemistry Laboratory, University of Sussex, Falmer, Brighton BN1 9QJ, UK. s.caddick@sussex.ac.uk
Bush
Hannah D
HD
D013449:Sulfonamides / Q000138:chemical synthesis*; D013451:Sulfonic Acids / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*; D005464:Fluorobenzenes; D005466:Fluorocarbons
D013449:Sulfonamides; D013451:Sulfonic Acids; D014753:Vinyl Compounds; C478988:pentafluorophenyl vinylsulfonate; D005464:Fluorobenzenes; D005466:Fluorocarbons