New synthesis of beta-sultams from pentafluorophenyl sulfonates.
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].
Lewis
Alexandra K de K
AK
The Christopher Ingold Laboratories, Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, UK.
Mok
B James
BJ
Tocher
Derek A
DA
Wilden
Jonathan D
JD
Caddick
Stephen
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D003500:Cyclization; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis*; D013451:Sulfonic Acids / Q000737:chemistry
D000900:Anti-Bacterial Agents; D013449:Sulfonamides; D013451:Sulfonic Acids; C480101:beta-sultam