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Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls

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  • Hui Yang

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

  • Huai-Ri Sun

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

  • Rui-Qing He

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

  • Le Yu

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

  • Wei Hu

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

  • Jie Chen

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

  • Sen Yang

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

  • Gong-Gu Zhang

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

  • Ling Zhou

    (National Demonstration Center for Experimental Chemistry Education, Northwest University)

Abstract

The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones.

Suggested Citation

  • Hui Yang & Huai-Ri Sun & Rui-Qing He & Le Yu & Wei Hu & Jie Chen & Sen Yang & Gong-Gu Zhang & Ling Zhou, 2022. "Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-28211-0
    DOI: 10.1038/s41467-022-28211-0
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