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Gold(I)-Catalyzed Synthesis of Furopyrans: Insight into Hetero-Diels–Alder Reactions

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    Gold(I)-Catalyzed Synthesis of Furopyrans: Insight into Hetero-Diels–Alder Reactions
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    • Romain Pertschi
      Romain Pertschi
      CNRS, Laboratoire d’Innovation Thérapeutique, UMR 7200, Université de Strasbourg, 67000 Strasbourg, France
      More by Romain Pertschi
    • Patrick Wagner
      Patrick Wagner
      CNRS, Laboratoire d’Innovation Thérapeutique, UMR 7200, Université de Strasbourg, 67000 Strasbourg, France
      More by Patrick Wagner
    • Nayan Ghosh
      Nayan Ghosh
      CNRS, Laboratoire d’Innovation Thérapeutique, UMR 7200, Université de Strasbourg, 67000 Strasbourg, France
      More by Nayan Ghosh
    • Vincent Gandon*
      Vincent Gandon
      Institut de Chimie Moléculaire et des Matériaux d’Orsay, CNRS UMR 8182, Université Paris-Sud, Bâtiment 420, 91405 Orsay, France
      Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, Route de Saclay, 91128 Palaiseau, France
      *E-mail: [email protected]
      More by Vincent Gandon
      Orcidhttp://orcid.org/0000-0003-1108-9410
    • Gaëlle Blond*
      Gaëlle Blond
      CNRS, Laboratoire d’Innovation Thérapeutique, UMR 7200, Université de Strasbourg, 67000 Strasbourg, France
      *E-mail: [email protected]
      More by Gaëlle Blond
      Orcidhttp://orcid.org/0000-0001-9144-0295
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    Organic Letters

    Cite this: Org. Lett. 2019, 21, 15, 6084–6088
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    https://doi.org/10.1021/acs.orglett.9b02228
    Published July 12, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    We report herein the synthesis of complex molecules containing furopyran cores through a gold(I)-catalyzed hetero-Diels–Alder cascade reaction. During this process, the diene and the dienophile are produced concomitantly by the action of a single catalyst from a single starting material. Moreover, six bonds, four heterocycles, and four controlled stereogenic centers are formed in a one-step operation. DFT calculations provide the mechanistic basis of this unprecedented reaction.

    Copyright © 2019 American Chemical Society

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    Organic Letters

    Cite this: Org. Lett. 2019, 21, 15, 6084–6088
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.9b02228
    Published July 12, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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