Dimethyl Malonate/LHMDS System as a New Protocol for Generating Methyl Formate Anion (-COOMe) in the Condensed-Phase.

Abstract The treatment of dimethyl malonate with LHMDS in anhydrous THF (condensed-phase) generates, in addition to the expected corresponding lithium enolate, methyl formate anion (or methoxycarbonyl anion, − COOMe) which can react with several electrophiles to give corresponding methoxycarbonyl derivatives by nucleophilic substitution reaction.