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The Catalytic Asymmetric Knoevenagel Condensation

Authors

  • Anna Lee,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
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  • Dr. Anna Michrowska,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
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  • Dr. Sarah Sulzer-Mosse,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
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  • Prof. Dr. Benjamin List

    Corresponding author
    1. Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
    • Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
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  • Generous support from the Max-Planck-Society, the DFG (Priority Program Organocatalysis SPP1179), and the Fonds der Chemischen Industrie is gratefully acknowledged. We also thank our HPLC and GC departments for their support.

Abstract

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116 years after the discovery of the Knoevenagel condensation, the first catalytic asymmetric variant has been developed. Dynamic kinetic resolution in the reaction of α-branched aldehydes with malonates in the presence of a newly designed and readily available modified cinchona amine catalyst gives the corresponding alkylidene malonates in high enantioselectivity (see scheme).

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