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Enantiocontrolled Synthesis of β-Branched α-Amino Acids by Using CuI-Catalyzed 1,4-Addition of Glycine Imines to β-Substituted gem-Diactivated Olefins

Authors

  • Jorge Hernández-Toribio,

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid (UAM), Facultad de Ciencias, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 91-497-3966
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  • Dr. Ramón Gómez Arrayás,

    Corresponding author
    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid (UAM), Facultad de Ciencias, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 91-497-3966
    • Departamento de Química Orgánica, Universidad Autónoma de Madrid (UAM), Facultad de Ciencias, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 91-497-3966
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  • Prof. Dr. Juan C. Carretero

    Corresponding author
    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid (UAM), Facultad de Ciencias, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 91-497-3966
    • Departamento de Química Orgánica, Universidad Autónoma de Madrid (UAM), Facultad de Ciencias, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 91-497-3966
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Abstract

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Branching out! The catalytic asymmetric conjugate addition of glycinate Schiff bases to β-substituted gem-diactivated Michael acceptors under proton transfer conditions gives a variety of β-branched α-amino acids (see scheme; Dpm=diphenylmethylene, EWG=electron-withdrawing group) with excellent levels of diastereo- (typically syn/anti >90:10) and enantiocontrol (90–99 % ee).

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