Diastereoselective Electrochemical Carboxylation of Chiral α-Bromocarboxylic Acid Derivatives: An Easy Access to Unsymmetrical Alkylmalonic Ester Derivatives1

M Feroci, M Orsini, L Palombi, G Sotgiu…

Index: Feroci, Marta; Orsini, Monica; Palombi, Laura; Sotgiu, Giovanni; Colapietro, Marcello; Inesi, Achille Journal of Organic Chemistry, 2004 , vol. 69, # 2 p. 487 - 494

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Citation Number: 23

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 ...