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An exo- and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides with Alkylidene Malonates Catalyzed by a N,O-Ligand/Cu(OAc)2-Derived Chiral Complex

Authors

  • Ming Wang,

    1. School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China), Fax: (+86) 21-6425-2431
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  • Zheng Wang,

    1. School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China), Fax: (+86) 21-6425-2431
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  • Yu-Hua Shi,

    1. School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China), Fax: (+86) 21-6425-2431
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  • Prof. Xiao-Xin Shi,

    1. School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China), Fax: (+86) 21-6425-2431
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  • Dr. John S. Fossey,

    1. School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China), Fax: (+86) 21-6425-2431
    2. School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT (UK)
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  • Prof. Wei-Ping Deng

    Corresponding author
    1. School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China), Fax: (+86) 21-6425-2431
    • School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China), Fax: (+86) 21-6425-2431
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  • This work was supported by the Shanghai Committee of Science and Technology (06J14023, 09JC1404500) and “111” Project (No. B07023), and the Natural Science Foundation of China for young foreign scientists (No. 21050110426).

Abstract

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Anexo-lent catalyst: An N,O-ligand/Cu(OAc)2 derived chiral complex is an excellent catalyst for inducing asymmetry in the catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides with various alkylidene malonates. A series of highly functionalized exo-pyrrolidines were obtained in excellent yields (80–99 %) and enantioselectivities (91–99 % ee; see scheme; M.S.: molecular sieve).

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