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New synthesis of beta-sultams from pentafluorophenyl sulfonates
Journal article   Peer reviewed

New synthesis of beta-sultams from pentafluorophenyl sulfonates

Alexandra K de K Lewis, B James Mok, Derek A Tocher, Jonathan D Wilden and Stephen Caddick
Organic letters, Vol.8(24), pp.5513-5515
23/11/2006
PMID: 17107060

Abstract

Anti-Bacterial Agents - chemical synthesis Crystallography, X-Ray Cyclization Stereoisomerism Sulfonamides - chemical synthesis Sulfonic Acids - chemistry
A stereoselective one-pot synthesis of substituted 1,2-thiazetidine 1,1-dioxides (beta-sultams) has been achieved from heterocyclic pentafluorophenyl (PFP) sulfonates. Mild N-O bond cleavage of isoxazolidines followed by intramolecular cyclization of the amine onto the PFP demonstrates the potential utility for using the PFP sulfonate as a valuable precursor to sulfonamides. [reaction: see text].

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