Thallium (III)-Mediated Allylation of Alcohols and Carboxylic Acids : Umpolung of Reactivity of Allylmetal (Group IVb) Compounds

Abstract

A new general method for the synthesis of allyl ethers and allyl acetates is described. Allylmetal (group IVb) compounds, on treatment with thallium (III) salts in alcohols or acetic acid, gave the corresponding allyl ethers or allyl acetates in good yields. The reaction was successfully applied to the synthesis of the 6-membered cyclic ether 20 via the intramolecular, thallium (III)-mediated allylation reaction of the allylsilane 18.