Benvenuti nell'Anagrafe della Ricerca d'Ateneo
La valutazione delle attività di ricerca che si svolgono nelle università ha assunto un'importanza rilevante sia per l'intero sistema universitario sia all'interno di ogni singolo ateneo. Roma Tre si è quindi dotata di idonei strumenti informativi in grado di supportare al meglio le azioni di monitoraggio e di valutazione delle attività di ricerca svolte nei propri dipartimentied ha realizzato una Anagrafe della Ricerca di Ateneo.
EnglishThe diastereoselective electrochemical carboxylation of chiral N-(2-bromoacyl)oxazolidin-2-ones has been studied. This reaction was carried out by cathodic reduction of the C-Br bond, in the presence of carbon dioxide, followed by treatment with diazomethane. The yields and the diastereomeric ratio of the two epimeric alkylmalonic acid derivatives are strongly affected by various factors: solvent-supporting electrolyte system, temperature, electrode material, electrolysis conditions, oxazolidinone moiety. The higher yields (88%) were obtained starting from N-(2-bromopropionyl)4R-phenyloxazolidin-2-one la, but with poor diastereoselectivity (61:39). The two epimers were easily separated by flash chromatography. The best results were achieved using a different chiral auxiliary: Oppolzer's camphor sultam. Starting from 1j a good yield in carboxylated product was obtained (80%) with excellent diastereoselectivity (98:2). These chiral alkylmalonic acid derivatives are valuable building blocks in the synthesis of molecules with biological activity and of chiral propane-1,3-diols derivatives.
FEROCI M., ORSINI M., PALOMBI L., SOTGIU G, COLAPIETRO M., & INESI A. (2004). Diastereoselective electrochemical carboxylation of chiral ?-bromocarboxylic acid derivatives: an easy access to unsymmetrical alkylmalonic ester derivatives. JOURNAL OF ORGANIC CHEMISTRY, 69(2), 487-494.
| Titolo: | Diastereoselective electrochemical carboxylation of chiral ?-bromocarboxylic acid derivatives: an easy access to unsymmetrical alkylmalonic ester derivatives |
| Autori: | |
| Data di pubblicazione: | 2004 |
| Rivista: | |
| Citazione: | FEROCI M., ORSINI M., PALOMBI L., SOTGIU G, COLAPIETRO M., & INESI A. (2004). Diastereoselective electrochemical carboxylation of chiral ?-bromocarboxylic acid derivatives: an easy access to unsymmetrical alkylmalonic ester derivatives. JOURNAL OF ORGANIC CHEMISTRY, 69(2), 487-494. |
| Abstract: | The diastereoselective electrochemical carboxylation of chiral N-(2-bromoacyl)oxazolidin-2-ones has been studied. This reaction was carried out by cathodic reduction of the C-Br bond, in the presence of carbon dioxide, followed by treatment with diazomethane. The yields and the diastereomeric ratio of the two epimeric alkylmalonic acid derivatives are strongly affected by various factors: solvent-supporting electrolyte system, temperature, electrode material, electrolysis conditions, oxazolidinone moiety. The higher yields (88%) were obtained starting from N-(2-bromopropionyl)4R-phenyloxazolidin-2-one la, but with poor diastereoselectivity (61:39). The two epimers were easily separated by flash chromatography. The best results were achieved using a different chiral auxiliary: Oppolzer's camphor sultam. Starting from 1j a good yield in carboxylated product was obtained (80%) with excellent diastereoselectivity (98:2). These chiral alkylmalonic acid derivatives are valuable building blocks in the synthesis of molecules with biological activity and of chiral propane-1,3-diols derivatives. |
| Handle: | http://hdl.handle.net/11590/143311 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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