Ester-Mediated Nucleophilic Aromatic Substitution of 2,3-Alkylidenedioxybenzoic Esters by Aryl Lithium Reagents

Treatment of 2,6-di-tert-butyl-4-methylphenyl 2,3-methylenedioxybenzoate with several aryllithium reagents in diethyl ether at 0 °C affords 6-hydroxy-1,1′-biphenyl-2-carboxylates in good to excellent yields. Reaction of an (S)-(−)-2,3-ethylidenedioxybenzoic ester with 2-methoxy-4,6-dimethylphenyllithium induces R axial twist with not less than 81% diastereoselectivity in the biphenyl coupling.