期刊
SYNLETT
卷 28, 期 2, 页码 225-230出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588895
关键词
asymmetric organocatalysis; cinchona alkaloids; halolactonization reaction; 3-substituted isobenzofuranones
资金
- CNRS
- Chevreul Institute [FR 2638]
- Ministere de l'Enseignement Superieur et de la Recherche
- Region Nord - Pas de Calais
- FEDER
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.
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