Palladium-Catalyzed Asymmetric Decarboxylation of 5-Vinyloxazolidine-2,4-Diones Triggering the Dearomatization of Electron-Deficient Indoles for the Synthesis of Chiral Highly Functionalized Pyrroloindolines
Pei‐Hao Dou, Xiaohui Fu, Yan Chen, Zhen-Zhen Ge, Ming‐Qiang Zhou, Zhen‐Hua Wang, Yong You, Lei Yang, Yanping Zhang, Jian‐Qiang Zhao, Wei‐Cheng Yuan
Abstract
causes the decarboxylation of 5-vinyloxazolidine-2,4-diones to generate amide-containing aza-π-allylpalladium 1,3-dipole intermediates, which are capable of triggering the dearomatization of 3-nitroindoles for diastereo- and enantioselective [3+2] cycloaddition, leading to the formation of a series of highly functionalized pyrroloindolines containing three contiguous stereogenic centers with excellent results (up to 99% yield, 88:12 dr, and 96% ee).
Topics & Concepts
ChemistryStereocenterDecarboxylationPhosphoramiditeEnantioselective synthesisCatalysisYield (engineering)AmidePalladiumLigand (biochemistry)Combinatorial chemistryCycloadditionOrganic chemistryStereochemistryReceptorMetallurgyMaterials scienceBiochemistryDNAOligonucleotideAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsSynthesis and Characterization of Pyrroles