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

A new electrochem. method for the mild generation of naked b-dicarbonyl deriv. enolates is disclosed. The electrolysis, under galvanostatic control, of a soln. of N-acetoacetyloxazolidin-2-ones/acetonitrile/tetraethylammonium perchlorate allowed the selective a-monoalkylation of the 1,3-dicarbonyl residue with a variety of alkyl halides in very good yields and short reaction times. More interestingly, no byproducts arising from either the electroredn. of the carbonyl functionalities or from nucleophilic cyanomethyl anion attack were detected.