Synthesis of 3,3-Dialkyl-Substituted Isoindolinones Enabled by Nickel-Catalyzed Reductive Dicarbofunctionalization of Enamides
Fang Ke, Wenyi Huang, Chunxiao Shan, Jingping Qü, Yifeng Chen
Abstract
Herein we report the nickel-catalyzed reductive dicarbofunctionalization of 1,1-disubstituted enamides with unactivated alkyl iodides to access the 3,3-dialkyl-substituted isoindolinone frameworks. This tandem cyclization/reductive coupling protocol exhibits broad functional group tolerance under mild conditions. The utilization of commercially accessible chiral Bn-Biox ligand allows excellent enantioselectivities to forge the tetrasubstituted stereocenters.
Topics & Concepts
ChemistryStereocenterCatalysisCombinatorial chemistryTandemReductive eliminationNickelLigand (biochemistry)Functional groupAlkylOrganic chemistryEnantioselective synthesisReceptorBiochemistryPolymerComposite materialMaterials scienceCatalytic C–H Functionalization MethodsSynthesis and pharmacology of benzodiazepine derivativesAdvanced Synthetic Organic Chemistry