Palladium-Catalyzed Regio- and Stereoselective Cross-Coupling of Vinylethylene Carbonates with Ketimine Esters to Generate (<i>Z</i>)-Tri- and Tetra-substituted Allylic Amino Acid Derivatives
Miaolin Ke, Zhigang Liu, Guanxin Huang, Jiaqi Wang, Yuan Tao, Fen‐Er Chen
Abstract
Herein we report the palladium-catalyzed regio- and stereoselective cross-coupling of vinylethylene carbonates with ketimine esters to construct allylic amino acid scaffolds. This operationally simple protocol furnished (Z)-tri- and tetra-substituted allylic amino acid derivatives in good to excellent yields with distinguished geometric control under mild reaction conditions and proved to be sufficient in large-scale synthesis while retaining excellent reactivity and stereoselectivity, highlighting the practical value of this transformation.
Topics & Concepts
StereoselectivityChemistryAllylic rearrangementPalladiumCatalysisTetraReactivity (psychology)Coupling reactionStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryAlternative medicineMedicinePathologyAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms