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Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes

Authors

  • Han Yong Bae,

    1. Department of Chemistry, Sungkyunkwan University, 300, Cheoncheon, Jangan, Suwon, 440-746 (Korea)
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  • Jae Hun Sim,

    1. Department of Chemistry, Sungkyunkwan University, 300, Cheoncheon, Jangan, Suwon, 440-746 (Korea)
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  • Ji-Woong Lee,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
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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)
    • Benjamin List, Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)

      Choong Eui Song, Department of Chemistry, Sungkyunkwan University, 300, Cheoncheon, Jangan, Suwon, 440-746 (Korea)

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  • Prof. Dr. Choong Eui Song

    Corresponding author
    1. Department of Chemistry, Sungkyunkwan University, 300, Cheoncheon, Jangan, Suwon, 440-746 (Korea)
    • Benjamin List, Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)

      Choong Eui Song, Department of Chemistry, Sungkyunkwan University, 300, Cheoncheon, Jangan, Suwon, 440-746 (Korea)

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  • We gratefully acknowledge the financial support provided by the Max Planck Society, the European Research Council (Advanced grant “High Performance Lewis Acid Organocatalysis, HIPOCAT” to B.L.), and the Ministry of Education, Science and Technology (the Basic Science Research Programme (NRF-20090085824, MEST), Priority Research Centres Programme (NRF-2012-R1A6A1040282, MEST), SRC programme (2012-0000647, MEST), and the WCU programme (R31-2008-10029, MEST). H.Y.B. acknowledges Global Ph. D. Fellowship.

Abstract

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Der Cinchona-Sulfonamid-Organokatalysator 1 vermittelt die hoch enantioselektive biomimetische Aldolreaktion von Malonsäure-Halbthioestern mit vielfältigen Aldehyden unter Bildung von optisch aktiven β-Hydroxythioestern. Das Verfahren bewährte sich in Formalsynthesen der Antidepressiva (R)-Fluoxetin, (R)-Tomoxetin, (−)-Paroxetin und (R)-Duloxetin.

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