Perfluoroalkyl-Promoted Synthesis of Perfluoroalkylated Pyrrolidine-Fused Coumarins with Methyl β-Perfluoroalkylpropionates
Nan Qi Ren, Lingfeng Zhang, Yijie Hu, Xiaoli Wang, Zhen Deng, Jie Chen, Hongmei Deng, Hui Zhang, Xiaojun Tang, Weiguo Cao
Abstract
Employing the methyl β-perfluoroalkylpropionate as the Michael acceptor, an efficient approach for the synthesis of perfluoroalkylated pyrrolidine-fused coumarins has been achieved. A tandem reaction involving [3 + 2] cycloaddition and intramolecular transesterification was proposed for the mechanism. The enhanced electrophilicity resulting from the strong electron-withdrawing ability of the perfluoroalkyl group was crucial for this tandem reaction.
Topics & Concepts
ChemistryPyrrolidineIntramolecular forceCycloadditionElectrophileTandemMichael reactionTransesterificationCascade reactionIntramolecular reactionPolar effectOrganic chemistryCombinatorial chemistryStereochemistryCatalysisComposite materialMaterials scienceFluorine in Organic ChemistrySynthesis and Biological EvaluationChemical Synthesis and Analysis