Palladium-catalyzed Heck reaction on 1-alkoxy-1,3-dienes: a regioselective gamma-arylation of alpha,beta-unsaturated carbonyl compounds

Org Lett. 2003 Oct 16;5(21):3815-7. doi: 10.1021/ol035258j.

Abstract

[reaction: see text] alpha,beta-Unsaturated acetals afford, in the presence of the LIC-KOR superbase, 1-alkoxybuta-1,3-dienes. These substrates cross couple with aryl derivatives in the presence of Pd catalyst (Heck conditions) in a regio- and stereoselective mode. With dialkyl acetals, the reaction affords arylated dienes; on the other hand, in the case of 1,3-dioxane derivatives, the final outcome of the process formally corresponds to the direct gamma-arylation reaction of the starting alpha,beta-unsaturated material.