Synthesis of functionalized sulfonamides via 1, 3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate

S Caddick, HD Bush

Index: Caddick, Stephen; Bush, Hannah D. Organic Letters, 2003 , vol. 5, # 14 p. 2489 - 2492

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Citation Number: 25

Abstract

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.