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Design and catalytic atroposelective synthesis of axially chiral isochromenone-indoles

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Abstract

The catalytic atroposelective synthesis of axially chiral isochromenone-indoles has been established by the strategy of designing homophthalic anhydride-based indole derivatives as a new type of indole-based platform molecules for dynamic kinetic resolution. By this strategy, a wide range of axially chiral isochromenone-indoles were synthesized in high yields with excellent enantioselectivities (up to 98% yield, 97% ee) via the catalytic asymmetric sulfonylation reaction of homophthalic anhydride-based indole derivatives with aryl sulfonyl chlorides under the catalysis of chiral quaternary ammonium salt as a phase-transfer catalyst

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Acknowledgements

This work was supported by the National Science Foundation of China (22125104, 21831007, 22101103) and the Natural Science Foundation of Jiangsu Province (BK20201018). We are grateful to Prof. Shu Zhang and Prof. Yinchun Jiao for their kind help in biological evaluation and theoretical calculation on the rotational barrier.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Research Center of Chiral Functional Heterocycles, School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116, China

    Qing-Qing Hang, Shu-Fang Wu, Shuang Yang, Xue Wang, Zhen Zhong, Yu-Chen Zhang & Feng Shi

  2. School of Petrochemical Engineering, Changzhou University, Changzhou, 213164, China

    Feng Shi

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  1. Qing-Qing Hang
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Correspondence to Yu-Chen Zhang or Feng Shi.

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Conflict of interest The authors declare no conflict of interest.

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Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Hang, QQ., Wu, SF., Yang, S. et al. Design and catalytic atroposelective synthesis of axially chiral isochromenone-indoles. Sci. China Chem. 65, 1929–1937 (2022). https://doi.org/10.1007/s11426-022-1363-y

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  • DOI: https://doi.org/10.1007/s11426-022-1363-y

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