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Organocatalytic Asymmetric Hydrolysis of Epoxides

Authors

  • Mattia Riccardo Monaco,

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

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

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  • Generous support by the Max-Planck-Society and the European Research Council (Advanced Grant “High Performance Lewis Acid Organocatalysis, HIPOCAT”) is gratefully acknowledged. We thank the members of our mass spectrometry department for their excellent service.

Abstract

The hydrolytic ring opening of epoxides is an important biosynthetic transformation and is also applied industrially. We report the first organocatalytic variant of this reaction, exploiting our recently discovered activation of carboxylic acids with chiral phosphoric acids via heterodimerization. The methodology mimics the enzymatic mechanism, which involves an enzyme-bound carboxylate nucleophile. A newly designed phosphoric acid catalyst displays high stereocontrol in the desymmetrization of meso-epoxides. The methodology shows wide generality with cyclic, acylic, aromatic, and aliphatic substrates. We also apply our method in the first highly enantioselective anti-dihydroxylation of simple olefins.

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