The First Allylation of Esters by an Allylsilane: One‐Pot Domino Synthesis of Triallylmethane Derivatives

Abstract

AbstractWe report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3–1.0 equiv. of titanium tetrachloride (TiCl4) at room temperature and leads in a multi‐step, one‐pot reaction to quaternary triallylmethane derivatives 5. The most efficient ester possessed two ortho‐methoxy substituents on the phenol ring. Molecular modelling revealed the ability of this compound to form a bidentate titanium complex, thus improving the steric accessibility of the ester carbonyl to nucleophilic attack.magnified image