3-unsaturated alkyl cephems from 3-triflyl cephems

Abstract From the Canadian patent

There is disclosed a process for the production of certain 3-hydrocarbyl-3-cephem derivatives wherein the hydrocarbyl group is selected from 1-alkenyl and conjugated and unconjugated 1-polyalkenyl, 1-alkynyl carbocyclic and, heterocyclic aryl, and carbocyclic and heterocyclic arylmethyl and, in the case of the 1-alkenyl and conjugated 1-polyalkenyl derivatives, with substantially complete stereospecificity, by coupling a 3-triflyloxy cephem with a hydrocarbyltributylstannane in the presence of bis(di-benzylideneacetonyl)-palladium, a phosphine and a metal, halide such as, for example zinc chloride. The, 3-unsaturated alkyl-3-cephem derivatives so-produced are useful as broad-spectrum …