Palladium‐Catalyzed (5+3) Annulation of 4‐Vinyl‐4‐Butyrolactones with C,N‐Cyclic Azomethine Imines: Construction of Eight‐Membered Ring
Sen Yang, Kuan Li, Yi Tang, Bing Zheng, Wei Wang, Yongjun Wu, Yumei Xiao, Hongchao Guo
Abstract
Abstract In this paper, we designed and synthesized 4‐vinyl‐4‐butyrolactone as a precursor to generate the zwitterionic allylpalladium intermediates, which behaved as five‐membered all‐carbon synthon in palladium‐catalyzed (5+3) annulation with azomethine imines, giving eight‐membered ring‐fused heterocycles (26 examples, 49% to 97% yield, >20:1 dr). magnified image
Topics & Concepts
AnnulationSynthonChemistryPalladiumRing (chemistry)CatalysisYield (engineering)Medicinal chemistryCombinatorial chemistryOrganic chemistryMaterials scienceMetallurgyCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry MethodsCyclopropane Reaction Mechanisms