Palladium(0)-catalysed cross-coupling reactions of α-alkoxyalkenylstannanes and α-alkoxyalkenylzincs

Abstract

α-Alkoxyalkenylstannanes prepared by the Pd⁰-catalysed hydrostannylation of 1 -alkoxyalk-1-ynes, undergo Pd⁰-catalysed Stille-type cross-coupling reactions with acid chlorides, aryl iodides and alkenyl trifluoromethanesulfonates. In the most complex case, an enol ether moiety was appended to a carbapenem nucleus. The coupling reaction was strongly dependent upon solvent, temperature, and added ligands. The method substantially extends the use of metallated enol ethers as nucleophilic acylation agents.