Synthesis of α-Quaternary β-Lactams via Copper-Catalyzed Enantioconvergent Radical C(sp3)−C(sp2) Cross-Coupling with Organoboronate Esters
Dr. Fu-Li Wang
School of Science and Institute of Scientific Research, Great Bay University, Dongguan, 523000 China
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Lin Liu
School of Science and Institute of Scientific Research, Great Bay University, Dongguan, 523000 China
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Chang-Jiang Yang
School of Science and Institute of Scientific Research, Great Bay University, Dongguan, 523000 China
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorCheng Luan
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorDr. Jing Yang
College of Health Science and Environmental Engineering, Shenzhen Technology University, Shenzhen, 518118 China
Search for more papers by this authorDr. Ji-Jun Chen
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorDr. Qiang-Shuai Gu
Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorCorresponding Author
Dr. Zhong-Liang Li
Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xin-Yuan Liu
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorDr. Fu-Li Wang
School of Science and Institute of Scientific Research, Great Bay University, Dongguan, 523000 China
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Lin Liu
School of Science and Institute of Scientific Research, Great Bay University, Dongguan, 523000 China
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Chang-Jiang Yang
School of Science and Institute of Scientific Research, Great Bay University, Dongguan, 523000 China
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorCheng Luan
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorDr. Jing Yang
College of Health Science and Environmental Engineering, Shenzhen Technology University, Shenzhen, 518118 China
Search for more papers by this authorDr. Ji-Jun Chen
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorDr. Qiang-Shuai Gu
Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorCorresponding Author
Dr. Zhong-Liang Li
Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xin-Yuan Liu
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055 China
Search for more papers by this authorAbstract
The copper-catalyzed enantioconvergent radical C(sp3)−C(sp2) cross-coupling of tertiary α-bromo-β-lactams with organoboronate esters could provide the synthetically valuable α-quaternary β-lactams. The challenge arises mainly from the construction of sterically congested quaternary stereocenters between the tertiary alkyl radicals and chiral copper(II) species. Herein, we describe our success in achieving such transformations through the utilization of a copper/hemilabile N,N,N-ligand catalyst to forge the sterically congested chiral C(sp3)−C(sp2) bond via a single-electron reduction/transmetalation/bond formation catalytic cycle. The synthetic potential of this approach is shown in the straightforward conversion of the corresponding products into many valuable building blocks. We hope that the developed catalytic cycle would open up new vistas for more enantioconvergent cross-coupling reactions.
Open Research
Data Availability Statement
The data that support the findings of this study are openly available in Cambridge Crystallographic Data Centre at https://www.ccdc.cam.ac.uk/structures/, reference number 2210247.
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