IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v14y2023i1d10.1038_s41467-023-43092-7.html
   My bibliography  Save this article

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
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-023-43092-7
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-023-43092-7?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    References listed on IDEAS

    as
    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.
    Full references (including those not matched with items on IDEAS)

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    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.

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Xiaosheng Yan & Jinlian Cao & Huan Luo & Zhao Li & Zexing Cao & Yirong Mo & Yun-Bao Jiang, 2024. "Heterochiral coupling to bilateral β-turn structured azapeptides bearing two remote chiral centers," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    2. Yuan Wang & Dian Niu & Guanghui Ouyang & Minghua Liu, 2022. "Double helical π-aggregate nanoarchitectonics for amplified circularly polarized luminescence," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    3. Debashis Mondal & Manzoor Ahmad & Bijoy Dey & Abhishek Mondal & Pinaki Talukdar, 2022. "Formation of supramolecular channels by reversible unwinding-rewinding of bis(indole) double helix via ion coordination," Nature Communications, Nature, vol. 13(1), pages 1-11, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-43092-7. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.