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Chiral Spiro Phosphoric Acid-Catalyzed Friedel–Crafts Conjugate Addition/Enantioselective Protonation Reactions

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    Research Article

    Chiral Spiro Phosphoric Acid-Catalyzed Friedel–Crafts Conjugate Addition/Enantioselective Protonation Reactions
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    • Yi-Pan Li
      Yi-Pan Li
      State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
      More by Yi-Pan Li
    • Zi-Qi Li
      Zi-Qi Li
      State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
      More by Zi-Qi Li
    • Biying Zhou
      Biying Zhou
      State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
      More by Biying Zhou
    • Mao-Lin Li
      Mao-Lin Li
      State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
      More by Mao-Lin Li
    • Xiao-Song Xue
      Xiao-Song Xue
      State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
      More by Xiao-Song Xue
      Orcidhttp://orcid.org/0000-0003-4541-8702
    • Shou-Fei Zhu*
      Shou-Fei Zhu
      State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
      *E-mail: [email protected]
      More by Shou-Fei Zhu
      Orcidhttp://orcid.org/0000-0002-6055-3139
    • Qi-Lin Zhou*
      Qi-Lin Zhou
      State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
      *E-mail: [email protected]
      More by Qi-Lin Zhou
      Orcidhttp://orcid.org/0000-0002-4700-3765
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    ACS Catalysis

    Cite this: ACS Catal. 2019, 9, 7, 6522–6529
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    https://doi.org/10.1021/acscatal.9b01502
    Published June 11, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Asymmetric Friedel–Crafts conjugate addition reactions that generate an α-chiral center are challenging because the configuration-determining step is a proton-transfer reaction of a highly active enol intermediate. Herein, we report a protocol for highly enantioselective Friedel–Crafts conjugate addition of indoles and pyrroles to exocyclic enones catalyzed by chiral spiro phosphoric acids. This protocol provides a straightforward, efficient approach to synthetically important indole-containing cyclic ketones with an α-chiral center and features with high yields (up to 99%) and high enantioselectivities (up to 98% ee) for a broad substrate scope. Density functional theory calculations suggest that the spiro phosphoric acid initially catalyzed the addition reaction by acting as a Brønsted acid and then catalyzed an enantioselective proton-transfer reaction of the enol intermediate by acting as a chiral proton-transfer shuttle. The enantiocontrol strategy described herein may be widely applicable to other addition reactions in which a proton transfer is the configuration-determining step.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscatal.9b01502.

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    • Metrical parameters for the structure (+)-4aa (CIF)

    • Metrical parameters for the structure (−)-5a (CIF)

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    Cited By

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    This article is cited by 59 publications.

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    ACS Catalysis

    Cite this: ACS Catal. 2019, 9, 7, 6522–6529
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acscatal.9b01502
    Published June 11, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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