Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated γ-Lactam
Xianqing Wu, Jingping Qü, Yifeng Chen
Abstract
Herein, we report a nickel-catalyzed reductive cross-coupling reaction of easily accessible 3-butenyl carbamoyl chloride with primary alkyl iodide to access the chiral α-alkylated pyrrolidinone with broad substrate scope and high enantiomeric excess. The current art of synthesis still remains challenging on the enantioselective α-monoalkylation of pyrrolidinones. The newly designed chiral 8-quinoline imidazoline ligand (Quinim) is crucial for maintaining the reactivity and enantioselectivity to ensure the reductive cyclization of monosubstituted alkenes for unprecedented synthesis of chiral non-aromatic heterocycles.
Topics & Concepts
ChemistryEnantioselective synthesisAlkylationCombinatorial chemistryLigand (biochemistry)IodideQuinolineCatalysisEnantiomerSubstrate (aquarium)Reactivity (psychology)NickelLactamOrganic chemistryGeologyMedicineReceptorBiochemistryAlternative medicineOceanographyPathologyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis