Palladium-catalyzed alkoxycarbonylation of conjugated enyne oxiranes: A diastereoselective method for the synthesis of 7-hydroxy-2,3,5-trienoates

Abstract

Palladium-catalyzed alkoxycarbonylative 1,5-substitution of conjugated enyne oxiranes provides a diastereoselective route to (E)-configured 7-hydroxy-2,3,5-trienoates. The reactions proceeded in a highly stereoselective manner, possibly through sequential formation of π-allylpalladium and σ-vinylallenyl palladium complexes. The major diastereomeric form of the product is determined by the configuration of the alkenyl moiety of the substrate.