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EnglishA 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.
http://hdl.handle.net/11697/11753| Titolo: | Electrochemical generation of tetraethylammonium N-acetoacetyloxazolidin-2-one enolates: an easy access to alpha-alkylated acetoacetic derivatives |
| Autori interni: | ROSSI, LEUCIO |
| Data di pubblicazione: | 2002 |
| Rivista: | TETRAHEDRON LETTERS |
| Abstract: | 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. |
| Handle: | http://hdl.handle.net/11697/11753 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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