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

A new electrochemical method for the mild generation of naked β-dicarbonyl derivative enolates is disclosed. The electrolysis, under galvanostatic control, of a solution of N-acetoacetyloxazolidin-2-ones/acetonitrile/tetraethylammonium perchlorate allowed the selective α-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.