Dynamic One-Pot Three-Component Catalytic Asymmetric Transformation by Combination of Hydrogen-Bond-Donating and Amine Catalysts

Authors

  • Dr. Shuangzheng Lin,

    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
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  • Luca Deiana,

    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
    2. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
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  • Dr. Gui-Ling Zhao,

    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
    2. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
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  • Prof. Dr. Junliang Sun,

    1. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
    2. Department of Structural Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
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  • Prof. Dr. Armando Córdova

    Corresponding author
    1. Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
    2. Berzelii Center EXSELENT on Porous Materials, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
    3. Department of Natural Sciences, Engineering and Mathematics, Mid Sweden University, 85170 Sundsvall (Sweden), Fax: (+46) 8-154-908
    • Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden)
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  • We gratefully acknowledge the Swedish National Research council and Wenner-Gren-Foundation for financial support. The Berzelii Center EXSELENT is financially supported by VR and the Swedish Governmental Agency for Innovation Systems (VINNOVA).

Abstract

original image

In control: The first dynamic one-pot three-component asymmetric transformation between aldehydes, protected α-cyanoglycine esters, and enals catalyzed by a combination of a simple hydrogen-bond-donating catalyst and a chiral amine catalyst is disclosed. Polysubstituted proline derivatives, which have a quaternary α stereocenter, were synthesized with high endo-, diastereo-, and enantioselectivities (93–99 % ee).

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