Nickel/Quinim Enabled Asymmetric Carbamoyl-Acylation of Unactivated Alkenes
Xianqing Wu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
These authors contributed equally.
Search for more papers by this authorHaiyan Li
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
These authors contributed equally.
Search for more papers by this authorFeng He
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
Search for more papers by this authorJingping Qu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Yifeng Chen
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
E-mail: [email protected]Search for more papers by this authorXianqing Wu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
These authors contributed equally.
Search for more papers by this authorHaiyan Li
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
These authors contributed equally.
Search for more papers by this authorFeng He
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
Search for more papers by this authorJingping Qu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Yifeng Chen
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
Transition metal-catalyzed difunctionalization of tethered alkene has emerged as a prevailing tool for the expedient construction of synthetically valuable cyclic compounds. However, most efforts have been devoted to the reaction of styrene-type substrates due to their rigid scaffold and high reactivity. With respect to the difunctionalization of nonaromatic tethered olefin, especially the mono-substituted alkene, still remains largely underdeveloped. Herein, we disclose a nickel/Quinim complex and TBADT-cocatalyzed asymmetric carbamoyl-acylation of unactivated alkene tethered on nonaromatic carbamoyl chlorides with diverse aldehydes. The reaction exhibits broad substrate scope with good functional group tolerance, as well as high reaction efficiency and enantioselectivity. Both monosubstituted and 1,1-substituted alkenes can work well with either aliphatic or aromatic aldehydes under the current protocol, providing convenient access to an array of medicinally useful chiral γ-lactams derivatives bearing a convertible acyl functionality. This reaction showcases more application possibilities of the chiral Quinim ligand in the future asymmetric catalytic transformations.
Supporting Information
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