The effect of base and additive on the alkylation of methyl hippurate

Article abstract of DOI:10.1016/S0040-4020(01)88213-2

Contrary to a published report, C-alkylation of methyl hippurate requires two equivalents of base. The choice of additive (TMEDA or HMPA) influences the result. Deuteration of the enolate gives results which depend on both the deuterium source and the nature of the additive.