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Thermo-responsive chiral micelles as recyclable organocatalyst for asymmetric Rauhut-Currier reaction in water

Author

Listed:
  • Lei Xu

    (Jilin University
    Huaibei Normal University)

  • Li Zhou

    (Hefei University of Technology)

  • Yan-Xiang Li

    (Hefei University of Technology)

  • Run-Tan Gao

    (Jilin University)

  • Zheng Chen

    (Jilin University)

  • Na Liu

    (Jilin University)

  • Zong-Quan Wu

    (Jilin University)

Abstract

Developing eco-friendly chiral organocatalysts with the combined advantages of homogeneous catalysis and heterogeneous processes is greatly desired. In this work, a family of amphiphilic one-handed helical polyisocyanides bearing phosphine pendants is prepared, which self-assembles into well-defined chiral micelles in water and showed thermo-responsiveness with a cloud point of approximately 38.4 °C. The micelles with abundant phosphine moieties at the interior efficiently catalyze asymmetric cross Rauhut-Currier reaction in water. Various water-insoluble substrates are transferred to target products in high yield with excellent enantioselectivity. The yield and enantiomeric excess (ee) of the product generated in water are up to 90% and 96%, respectively. Meanwhile, the yields of the same R-C reaction catalyzed by the polymer itself in organic solvents is

Suggested Citation

  • Lei Xu & Li Zhou & Yan-Xiang Li & Run-Tan Gao & Zheng Chen & Na Liu & Zong-Quan Wu, 2023. "Thermo-responsive chiral micelles as recyclable organocatalyst for asymmetric Rauhut-Currier reaction in water," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-43092-7
    DOI: 10.1038/s41467-023-43092-7
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    References listed on IDEAS

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    1. Xiaosheng Yan & Kunshan Zou & Jinlian Cao & Xiaorui Li & Zhixing Zhao & Zhao Li & Anan Wu & Wanzhen Liang & Yirong Mo & Yunbao Jiang, 2019. "Single-handed supramolecular double helix of homochiral bis(N-amidothiourea) supported by double crossed C−I···S halogen bonds," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
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    1. Ran Chen & Ahmad Hammoud & Paméla Aoun & Mayte A. Martínez-Aguirre & Nicolas Vanthuyne & Régina Maruchenko & Patrick Brocorens & Laurent Bouteiller & Matthieu Raynal, 2024. "Switchable supramolecular helices for asymmetric stereodivergent catalysis," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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