Dynamic Kinetic Asymmetric Domino Oxa-Michael/Carbocyclization by Combination of Transition-Metal and Amine Catalysis: Catalytic Enantioselective Synthesis of Dihydrofurans

Authors

  • Dr. Shuangzheng Lin,

    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden), Fax: (+46) 8-154908
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  • Dr. Gui-Ling Zhao,

    Corresponding author
    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden), Fax: (+46) 8-154908
    2. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden)
    • Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden), Fax: (+46) 8-154908
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  • Luca Deiana,

    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden), Fax: (+46) 8-154908
    2. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden)
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  • Prof. Dr. Junliang Sun,

    1. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden)
    2. Department of Structural Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden)
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  • Dr. Qiong Zhang,

    1. Department of Theoretical Chemistry, School of Biotechnology, Royal Institute of Technology, Roslagstullsbacken 15, 10691 Stockholm (Sweden)
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  • Dr. Hans Leijonmarck,

    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden), Fax: (+46) 8-154908
    2. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden)
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  • Prof. Dr. Armando Córdova

    Corresponding author
    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden), Fax: (+46) 8-154908
    2. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden)
    3. Department of Natural Sciences, Engineering and Mathematics, Mid Sweden University, 851 70 Sundsvall (Sweden)
    • Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden), Fax: (+46) 8-154908
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Abstract

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Into the pot: A one-pot highly chemo- and enantioselective catalytic domino oxa-Michael/carbocyclization between α,β-unsaturated aldehydes and propargylic alcohols is presented. This dynamic kinetic transformation requires a combination of transition-metal and amine catalysis to afford functionalized dihydrofurans in good to high yields and up to 99.5:0.5 e.r.

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