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All-round catalytic and atroposelective strategy via dynamic kinetic resolution for N-/2-/3-arylindoles

Author

Listed:
  • Ahreum Kim

    (Sungkyunkwan University)

  • Chanhee Lee

    (Sungkyunkwan University)

  • Jayoung Song

    (Seoul National University)

  • Sang Kook Lee

    (Seoul National University)

  • Yongseok Kwon

    (Sungkyunkwan University)

Abstract

As the complexity of organic molecules utilized by mankind increases, the phenomenon of atropisomerism is more frequently encountered. While a variety of well-established methods enable the control of a stereogenic center, a catalytic method for controlling a stereogenic axis in one substrate is typically unavailable for controlling axial chirality in other substrates with a similar structure. Herein, we report o-amidobiaryl as a flexible platform for chiral phosphoric acid-catalyzed atroposelective dynamic kinetic resolution. To demonstrate our strategy, three distinct types of arylindoles were utilized and reacted intermolecularly with ketomalonate in the presence of chiral phosphoric acid. An investigation of 46 substrates having an aromatic ring in different positions yields the desired products with excellent enantioselectivities. Computational investigation into the origin of enantioselectivity highlights the importance of the NH group. Given the biological significance of indoles, antiproliferative effects have been investigated; our scaffold exhibits good efficacy in this regard.

Suggested Citation

  • Ahreum Kim & Chanhee Lee & Jayoung Song & Sang Kook Lee & Yongseok Kwon, 2023. "All-round catalytic and atroposelective strategy via dynamic kinetic resolution for N-/2-/3-arylindoles," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-41299-2
    DOI: 10.1038/s41467-023-41299-2
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    References listed on IDEAS

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    1. Corin C. Wagen & Spencer E. McMinn & Eugene E. Kwan & Eric N. Jacobsen, 2022. "Screening for generality in asymmetric catalysis," Nature, Nature, vol. 610(7933), pages 680-686, October.
    2. Hui Zhou & Yu Zhou & Han Yong Bae & Markus Leutzsch & Yihang Li & Chandra Kanta De & Gui-Juan Cheng & Benjamin List, 2022. "Organocatalytic stereoselective cyanosilylation of small ketones," Nature, Nature, vol. 605(7908), pages 84-89, May.
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