A new electrochemical method for the mild generation of naked -dicarbonyl derivative enolates is disclosed. The electrolysis, under galvanostatic control, of a solution of N -acetoacetyloxazolidin-2-ones/acetonitrile/tetraethylammonium per- chlorate allowed the selective -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 functional- ities or from nucleophilic cyanomethyl anion attack were detected
Electrochemical generation of tetraethylammonium N-acetoacetyloxazolidin-2-one enolates: an easy access to alpha-alkylated acetoacetic derivatives / Palombi, L.; Feroci, Marta; Orsini, M.; Rossi, L.; Inesi, Achille. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 43:(2002), pp. 2881-2884. [10.1016/S0040-4039(02)00464-1]
Electrochemical generation of tetraethylammonium N-acetoacetyloxazolidin-2-one enolates: an easy access to alpha-alkylated acetoacetic derivatives.
FEROCI, Marta;INESI, ACHILLE
2002
Abstract
A new electrochemical method for the mild generation of naked -dicarbonyl derivative enolates is disclosed. The electrolysis, under galvanostatic control, of a solution of N -acetoacetyloxazolidin-2-ones/acetonitrile/tetraethylammonium per- chlorate allowed the selective -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 functional- ities or from nucleophilic cyanomethyl anion attack were detectedI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
