Palladium-catalyzed alkoxycarbonylation of (Z)-2-En-4-yn carbonates leading to 2,3,5-trienoates

Abstract

Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.