Palladium-Catalysed Regio- and Stereoselective Arylative Substitution of Gamma,delta-Epoxy Esters and Amides by Sodium Tetraaryl Borates

Abstract

Palladium-catalysed reactions of gamma,delta-epoxy-alpha,beta-unsaturated esters and amides with NaBAr(4)reagents proceeded regio- and stereoselectively, producing allylic homoallyl alcohols with aryl-substituents in the allylic position for a wide range of substrates. AsPh(3)was found to be a competent ligand for the arylation reaction, whereas phosphine ligand/Lewis acidic organoboron combinations favoured the substitution reaction by oxygen nucleophiles (e.g.H2O, ROH).