IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v14y2023i1d10.1038_s41467-023-38488-4.html
   My bibliography  Save this article

Asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes by synergistic Pd/chiral primary amine catalysis

Author

Listed:
  • Chang You

    (Tsinghua University)

  • Mingying Shi

    (Beijing Normal University)

  • Xueling Mi

    (Beijing Normal University)

  • Sanzhong Luo

    (Tsinghua University)

Abstract

We herein describe an asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes with 1,3-enynes. A synergistic chiral primary amine/Pd catalyst was identified to facilitate the utilization of 1,3-enynes as atom-economic and achiral allene precursors. The synergistic catalysis enables the construction of all-carbon quaternary centers-tethered allenes bearing non-adjacent 1,3-axial central stereogenic centers in high level of diastereo- and enantio-selectivity. By switching the configurations of ligands and aminocatalysts, diastereodivergence can be achieved and any of the four diastereoisomers can be accessed in high diastereo- and enantio- selectivity.

Suggested Citation

  • Chang You & Mingying Shi & Xueling Mi & Sanzhong Luo, 2023. "Asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes by synergistic Pd/chiral primary amine catalysis," Nature Communications, Nature, vol. 14(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-38488-4
    DOI: 10.1038/s41467-023-38488-4
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-023-38488-4
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-023-38488-4?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. Shihua Song & Jing Zhou & Chunling Fu & Shengming Ma, 2019. "Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    2. Thien Phuc Le & Shinji Tanaka & Masahiro Yoshimura & Kazuhiko Sato & Masato Kitamura, 2022. "Stereodivergent dehydrative allylation of β-keto esters using a Ru/Pd synergistic catalyst," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    3. Shi-Liang Shi & Zackary L. Wong & Stephen L. Buchwald, 2016. "Copper-catalysed enantioselective stereodivergent synthesis of amino alcohols," Nature, Nature, vol. 532(7599), pages 353-356, April.
    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. Ruimin Lu & Qinglin Zhang & Chang Guo, 2023. "Catalytic stereodivergent allylic alkylation of 2-acylimidazoles for natural product synthesis," Nature Communications, Nature, vol. 14(1), pages 1-10, 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. Ruimin Lu & Qinglin Zhang & Chang Guo, 2023. "Catalytic stereodivergent allylic alkylation of 2-acylimidazoles for natural product synthesis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Qi Liu & Jian Zheng & Xue Zhang & Shengming Ma, 2022. "Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    3. Biao Chen & Wenhuan Huang & Guoqing Zhang, 2023. "Observation of Chiral-selective room-temperature phosphorescence enhancement via chirality-dependent energy transfer," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    4. Cong Fu & Ling He & Hui Xu & Zongpeng Zhang & Xin Chang & Yanfeng Dang & Xiu-Qin Dong & Chun-Jiang Wang, 2024. "Modular access to chiral bridged piperidine-γ-butyrolactones via catalytic asymmetric allylation/aza-Prins cyclization/lactonization sequences," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    5. 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.

    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_s41467-023-38488-4. 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.