Synthesis of Planar-Chiral [2.2]Paracyclophane-Based Oxazole-Pyrimidine Ligands and Application in Nickel-Catalyzed 1,2-Reduction of α,β-Unsaturated Ketones
Juan Wang
School of Chemistry, Dalian University of Technology, 2 Linggong Road, Dalian, Liaoning, 116024 China
Search for more papers by this authorQing-Xian Xie
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorXiang Li
School of Chemistry, Dalian University of Technology, 2 Linggong Road, Dalian, Liaoning, 116024 China
Search for more papers by this authorCorresponding Author
Chang-Bin Yu
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Yong-Gui Zhou
School of Chemistry, Dalian University of Technology, 2 Linggong Road, Dalian, Liaoning, 116024 China
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
E-mail: [email protected]; [email protected]Search for more papers by this authorJuan Wang
School of Chemistry, Dalian University of Technology, 2 Linggong Road, Dalian, Liaoning, 116024 China
Search for more papers by this authorQing-Xian Xie
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
Search for more papers by this authorXiang Li
School of Chemistry, Dalian University of Technology, 2 Linggong Road, Dalian, Liaoning, 116024 China
Search for more papers by this authorCorresponding Author
Chang-Bin Yu
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Yong-Gui Zhou
School of Chemistry, Dalian University of Technology, 2 Linggong Road, Dalian, Liaoning, 116024 China
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
The planar-chiral ligands have been widely applied as a class of unique and significant ligands in asymmetric catalysis. Among them, chiral [2.2]paracycyclophane has emerged as a privileged type of planar-chiral framework and has been utilized as an important toolbox due to their structural stability. Herein, we design and synthesize [2.2]paracyclophane-derived oxazole-pyrimidine ligands (abberviated as PYMCOX). These N,N-ligands with stable properties, rigid structure and large steric hindrance performed successfully in nickel-catalyzed asymmetric 1,2-reduction of α,β-unsaturated ketones, affording the chiral allylic alcohols with up to 99% yield and 99% ee. Meanwhile, this reduction reaction could be conducted on gram-scale without loss of activity and enantioselectivity, and the chiral ligand could be conveniently recovered with high yield.
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