Abstract
A strategy employing both ring-closing metathesis (RCM) and ring-opening metathesis polymerization (ROMP) as routes to synthesizing oligomeric sulfonamides is described. Amino acid-derived α,β-unsaturated γ-sultams, containing either exo-cyclic or γ- endo-cyclic stereogenic centers, are generated via RCM. These sultams undergo stereoselective Diels–Alder reactions to yield endo-norbornenyl sulfonamides as the major diastereomers. Subsequent ROMP rapidly produces sulfonamide-based oligomers.
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