Bifunctional Lewis Base Catalyzed Asymmetric <i>N</i>-Allylic Alkylation of 2-Hydroxypyridines
Fei-Ruo Zhang, Fanshu Cao, Kui Liu, Yiping He, Gen Luo, Zhishi Ye
Abstract
-alkylated 2-pyridones with up to 99% ee and 99% yield. Experimental and computational studies have revealed that the strong hydrogen bond interaction between the chiral Lewis base catalyst and 2-hydroxypyridines plays a crucial role in this reaction for the reactivity, chemoselectivity, and enantioselectivity.
Topics & Concepts
ChemistryLewis acids and basesTsuji–Trost reactionEnantioselective synthesisBifunctionalAlkylationCatalysisReactivity (psychology)Allylic rearrangementChemoselectivityMedicinal chemistryOrganic chemistryCombinatorial chemistryAlternative medicineMedicinePathologyAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods