Electrochemical generation of tetraethylammonium N-acetoacetyloxazolidin-2-one enolates: an easy access to alpha-alkylated acetoacetic derivatives

A new electrochemical method for the mild generation of naked beta-dicarbonyl derivative enolates is disclosed. The electrolysis, under galvanostatic control. of a solution of N-acetoacetyloxazolidin-2-ones acetonitrile tetraethylammonium perchlorate allowed the selective alpha-monoalkylation of the 1.3-dicarbonyl residue with a variety of alkyl halides, in very good yields and short reaction times. More interestingly. no by-products arising from either the electroreduction of the carbonyl functionalities or from nucleophilic cyanomethyl anion attack were detected.