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An enantioselective four-component reaction via assembling two reaction intermediates

Author

Listed:
  • Sifan Yu

    (Sun Yat-sen University)

  • Wenju Chang

    (Nanjing University)

  • Ruyu Hua

    (Sun Yat-sen University)

  • Xiaoting Jie

    (Sun Yat-sen University)

  • Mengchu Zhang

    (Sun Yat-sen University)

  • Wenxuan Zhao

    (Nanjing University)

  • Jinzhou Chen

    (Sun Yat-sen University)

  • Dan Zhang

    (Sun Yat-sen University)

  • Huang Qiu

    (Sun Yat-sen University)

  • Yong Liang

    (Nanjing University)

  • Wenhao Hu

    (Sun Yat-sen University)

Abstract

A reaction intermediate is a key molecular entity that has been used in explaining how starting materials converts into the final products in the reaction, and it is usually unstable, highly reactive, and short-lived. Extensive efforts have been devoted in identifying and characterizing such species via advanced physico-chemical analytical techniques. As an appealing alternative, trapping experiments are powerful tools in this field. This trapping strategy opens an opportunity to discover multicomponent reactions. In this work, we report various highly diastereoselective and enantioselective four-component reactions (containing alcohols, diazoesters, enamines/indoles and aldehydes) which involve the coupling of in situ generated intermediates (iminium and enol). The reaction conditions presented herein to produce over 100 examples of four-component reaction products proceed under mild reaction conditions and show high functional group tolerance to a broad range of substrates. Based on experimental and computational analyses, a plausible mechanism of this multicomponent reaction is proposed.

Suggested Citation

  • Sifan Yu & Wenju Chang & Ruyu Hua & Xiaoting Jie & Mengchu Zhang & Wenxuan Zhao & Jinzhou Chen & Dan Zhang & Huang Qiu & Yong Liang & Wenhao Hu, 2022. "An enantioselective four-component reaction via assembling two reaction intermediates," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34913-2
    DOI: 10.1038/s41467-022-34913-2
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    References listed on IDEAS

    as
    1. Qian Xiong & Shunxi Dong & Yushuang Chen & Xiaohua Liu & Xiaoming Feng, 2019. "Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    2. 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. Taoda Shi & Tianyuan Zhang & Jiying Yang & Yukai Li & Jirong Shu & Jingyu Zhao & Mengchu Zhang & Dan Zhang & Wenhao Hu, 2023. "Bifunctionality of dirhodium tetracarboxylates in metallaphotocatalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.

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