Synthesis of 3-norcephalosporin 1 was performed successfully by reaction of
either 3-trifluoromethylsulfonyloxy-Delta(3)-cephem 2, allenecarboxylate 3
or 3,4-disubstitued but-2-enoates 4 with copper(I) chloride and tributylti
n hydride in N-methylpyrrolidin-2-one (NMP). Generation and reactions of a
copper(I) hydride species in the copper(I) chloride-tributyltin hydride-NMP
or N,N-dimethylformamide (DMF) system are discussed.