We report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3-1.0 equiv. of titanium tetrachloride (TiCl 4 ) at room temperature and leads in a multistep, one-pot reaction to quaternary triallylmethane derivatives 5. The most efficient ester possessed two ortho-methoxy substituents on the phenol ring. Mo-lecular 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.
The First Allylation of Esters by an Allylsilane: One-Pot Domino Synthesis of Triallylmethane Derivatives. -The 2,6-dimethoxyphenyl ester group usually gives the best results in the title reaction. -(BANDI, C. K. R.; BELOSTOTSKII, A.; HASSNER*, A.; Adv.
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