Total Synthesis of (–)-Herbaric Acid through ...
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Article dans une revue scientifique: Article original
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Title :
Total Synthesis of (–)-Herbaric Acid through Organocatalyzed Asymmetric Halolactonization of Acrylate-Type Benzoic Acids
Author(s) :
Deniau, Eric [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Michon, Christophe [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Gelat, Fabien [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Lebrun, Stephane [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Henry, Natacha [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Agbossou-Niedercorn, Francine [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Michon, Christophe [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Gelat, Fabien [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Lebrun, Stephane [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Henry, Natacha [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Agbossou-Niedercorn, Francine [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Journal title :
Synlett
Volume number :
28
Pages :
225-230
Publication date :
2017
ISSN :
0936-5214
English keyword(s) :
asymmetric organocatalysis
cinchona alkaloids
halolactonization reaction
3-substituted isobenzofuranones
cinchona alkaloids
halolactonization reaction
3-substituted isobenzofuranones
HAL domain(s) :
Chimie/Catalyse
Chimie/Chimie de coordination
Chimie/Chimie inorganique
Chimie/Chimie de coordination
Chimie/Chimie inorganique
English abstract : [en]
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, ...
Show more >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 based 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.Show less >
Show more >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 based 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.Show less >
Language :
Anglais
Audience :
Internationale
Popular science :
Non
Administrative institution(s) :
ENSCL
Université de Lille
CNRS
Centrale Lille
Univ. Artois
Université de Lille
CNRS
Centrale Lille
Univ. Artois
Collections :
Research team(s) :
Catalyse et synthèse éco-compatible (CASECO)
Chimie du solide et matériaux du nucléaire
Matériaux hybrides (MATHYB)
Méthodologie organométallique pour la catalyse homogène (MOCAH)
Chimie du solide et matériaux du nucléaire
Matériaux hybrides (MATHYB)
Méthodologie organométallique pour la catalyse homogène (MOCAH)
Submission date :
2019-09-25T14:05:12Z
2019-10-09T12:44:23Z
2019-10-16T07:57:27Z
2023-12-01T08:11:23Z
2019-10-09T12:44:23Z
2019-10-16T07:57:27Z
2023-12-01T08:11:23Z
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