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Total synthesis of (–)-herbaric acid through organocatalyzed asymmetric halolactonization of acrylate-type benzoic acids.
1  Unité de Catalyse et de Chimie du Solide (UCCS) UMR CNRS 8181 - Axe CCM - Equipe CASECO


The total synthesis of ()-herbaric acid has been achieved through the stereoselective synthesis of 3-substituted isobenzofuranones with a new organocatalytic route. When combined with a catalytic amount of benzoic acid, quinidine thiocarbamate bifunctional catalysts have demonstrated their efficiency for the diastereoselective halolactonization reaction of acrylate-type benzoic acids bearing a chiral alkoxycarbonyl group on the carbon-carbon double bond. High diastereomeric excesses were obtained thanks to a positive match effect between the (+)-menthyl ester group and the chiral organocatalyst.

Keywords: Asymmetric organocatalysis, Cinchona alkaloids, halolactonization reaction, 3-substituted isobenzofuranones