Issue 7, 2005
From the journal:

Organic & Biomolecular Chemistry

Stereoselective electrochemical carboxylation: 2-phenylsuccinates from chiral cinnamic acid derivatives†

Monica Orsini,a   Marta Feroci,*a   Giovanni Sotgiub  and  Achille Inesi*c  

* Corresponding authors

a Dip. Ingegneria Chimica, Materiali, Materie Prime e Metallurgia, Università “La Sapienza”, via Castro Laurenziano, 7, Roma, Italy
E-mail: marta.feroci@uniroma1.it
Fax: +39 06 49766749
Tel: +39 06 49766563

b Dipartimento di Elettronica Applicata, Università di Roma Tre, Via Vasca Navale, 84, Roma, Italy

c Dip. Chimica, Ingegneria Chimica e Materiali, Università degli Studi, Monteluco di Roio, L'Aquila, Italy
E-mail: inesi@ing.univaq.it

Abstract

Chiral 2-phenyl succinic ester derivatives have been obtained under mild conditions, in short times and with satisfactory yields by electrochemical reduction of chiral cinnamic acid derivatives under a CO2 atmosphere. When 4R-(diphenylmethyl)-oxazolidin-2-one was used as a chiral auxiliary the two diastereoisomers could be easily separated by flash chromatography and the R-isomer was obtained as major product.

Graphical abstract: Stereoselective electrochemical carboxylation: 2-phenylsuccinates from chiral cinnamic acid derivatives

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Article information

DOI
https://doi.org/10.1039/B500570A
Article type
Paper
Submitted
13 Jan 2005
Accepted
02 Feb 2005
First published
23 Feb 2005

Org. Biomol. Chem., 2005,3, 1202-1208

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Stereoselective electrochemical carboxylation: 2-phenylsuccinates from chiral cinnamic acid derivatives

M. Orsini, M. Feroci, G. Sotgiu and A. Inesi, Org. Biomol. Chem., 2005, 3, 1202 DOI: 10.1039/B500570A

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