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Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides

Author

Listed:
  • Jianjian Liu

    (Guizhou University)

  • Mali Zhou

    (Guizhou University)

  • Rui Deng

    (Guizhou University)

  • Pengcheng Zheng

    (Guizhou University)

  • Yonggui Robin Chi

    (Guizhou University
    Nanyang Technological University)

Abstract

Conformational isomerization can be guided by weak interactions such as chalcogen bonding (ChB) interactions. Here we report a catalytic strategy for asymmetric access to chiral sulfoxides by employing conformational isomerization and chalcogen bonding interactions. The reaction involves a sulfoxide bearing two aldehyde moieties as the substrate that, according to structural analysis and DFT calculations, exists as a racemic mixture due to the presence of an intramolecular chalcogen bond. This chalcogen bond formed between aldehyde (oxygen atom) and sulfoxide (sulfur atom), induces a conformational locking effect, thus making the symmetric sulfoxide as a racemate. In the presence of N–heterocyclic carbene (NHC) as catalyst, the aldehyde moiety activated by the chalcogen bond selectively reacts with an alcohol to afford the corresponding chiral sulfoxide products with excellent optical purities. This reaction involves a dynamic kinetic resolution (DKR) process enabled by conformational locking and facile isomerization by chalcogen bonding interactions.

Suggested Citation

  • Jianjian Liu & Mali Zhou & Rui Deng & Pengcheng Zheng & Yonggui Robin Chi, 2022. "Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32428-4
    DOI: 10.1038/s41467-022-32428-4
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    References listed on IDEAS

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    1. Alison E. Wendlandt & Prithvi Vangal & Eric N. Jacobsen, 2018. "Quaternary stereocentres via an enantioconvergent catalytic SN1 reaction," Nature, Nature, vol. 556(7702), pages 447-451, April.
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    Cited by:

    1. Minlong Wang & Jiaman Hou & Hainam Do & Chao Wang & Xiaohe Zhang & Ying Du & Qixin Dong & Lijun Wang & Ke Ni & Fazheng Ren & Jie An, 2024. "Intramolecular chalcogen bonding activated SuFEx click chemistry for efficient organic-inorganic linking," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    2. Meihui Liu & Xiao Han & Hao Chen & Qian Peng & Hui Huang, 2023. "A molecular descriptor of intramolecular noncovalent interaction for regulating optoelectronic properties of organic semiconductors," Nature Communications, Nature, vol. 14(1), pages 1-11, December.

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