Synthesis of 4-Unsubstituted β-Lactams via Dithiocarbonimidates

Article abstract of DOI:10.1055/s-1987-28144

Cycloaddition of dithiocarbonimidate 1 to the ketene generated in situ from phenoxyacetylchloride in the presence of triethylamine affords the 4-dithioalkyl-2-azetidinones 2 in good yields.Facile conversion of 2 to the 4-unsubstituted β-lactams 3 can be accomplished by desulfurization with Raney-Nickel.Formation of several interesting products during attempts to bring a carbonyl function at C-4 in 2 has also been described.