Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis
Zibo Bai, Heng Zhang, Hao Wang, Hanrui Yu, Gong Chen, Gang He
Abstract
An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed. The reaction uses amide-linked aminoquinoline as the directing group, 4-alkyl Hantzsch esters as the donor of alkyl radicals, and rarely used biaryl diphosphine oxide as a chiral ligand. β-lactams featuring two contiguous stereocenters at Cβ and the β substituent can be obtained in good yield with excellent enantioselectivity. Mechanistic studies indicate that a nucleophilic addition of the alkyl radical to CuII-coordinated alkene is the enantio-determining step.
Topics & Concepts
ChemistryEnantioselective synthesisAlkeneStereocenterAlkylSubstituentAmideNucleophileCatalysisLigand (biochemistry)Yield (engineering)Combinatorial chemistryMedicinal chemistryOrganic chemistryMetallurgyMaterials scienceReceptorBiochemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions