Issue 6, 2014
From the journal:

RSC Advances

Stereoselective synthesis of conjugated α-Z/γ-E and α-Z/γ-Z dienoic acids. Kinetic torquoselectivity versus thermodynamic control†

Jyoti Agarwal,a   Ouahiba Bayounes,a   Serge Thorimbert*a  and  Luc Dechoux*a  

* Corresponding authors

a UPMC Univ Paris 06. Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, BP43, 75005 Paris, France
E-mail: luc.dechoux@upmc.fr, serge.thorimbert@upmc.fr
Fax: +33 144273056
Tel: +33 144273084

Abstract

The stereoselective synthesis of conjugated (α-Z/γ-E)-(α-Z/γ-Z)-dienoic acids 4 and 4′ is described. It is based on the regio- and stereoselective addition of Grignard reagents to methylcoumalate. The origin of the stereocontrol is discussed.

Graphical abstract: Stereoselective synthesis of conjugated α-Z/γ-E and α-Z/γ-Z dienoic acids. Kinetic torquoselectivity versus thermodynamic control

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Article information

DOI
https://doi.org/10.1039/C3RA45309J
Article type
Communication
Submitted
23 Sep 2013
Accepted
14 Oct 2013
First published
21 Oct 2013

RSC Adv., 2014,4, 2772-2775

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Stereoselective synthesis of conjugated α-Z/γ-E and α-Z/γ-Z dienoic acids. Kinetic torquoselectivity versus thermodynamic control

J. Agarwal, O. Bayounes, S. Thorimbert and L. Dechoux, RSC Adv., 2014, 4, 2772 DOI: 10.1039/C3RA45309J

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