IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v15y2024i1d10.1038_s41467-024-46376-8.html
   My bibliography  Save this article

N-Heterocyclic carbene-catalyzed enantioselective synthesis of planar-chiral cyclophanes via dynamic kinetic resolution

Author

Listed:
  • Jiayan Li

    (Beijing Normal University)

  • Ziyang Dong

    (Beijing Normal University)

  • Yang Chen

    (Beijing University of Chemical Technology)

  • Zhanhui Yang

    (Beijing University of Chemical Technology)

  • Xinen Yan

    (Beijing Normal University)

  • Meng Wang

    (Beijing Normal University)

  • Chenyang Li

    (Beijing Normal University)

  • Changgui Zhao

    (Beijing Normal University)

Abstract

Planar-chiral cyclophanes have gained considerable concerns for drug discovery due to their unique conformational strain and 3D structure. However, the enantioselective synthesis of planar-chiral cyclophanes is a long-standing challenge for the synthetic community. We herein describe an N-heterocyclic carbene (NHC)-catalyzed asymmetric construction of planar-chiral cyclophanes. This transformation occurs through a dynamic kinetic resolution (DKR) process to convert racemic substrates into planar-chiral macrocycle scaffolds in good to high yields with high to excellent enantioselectivities. The ansa chain length and aromatic ring substituent size is crucial to achieve the DKR approach. Controlled experiments and DFT calculations were performed to clarify the DKR process.

Suggested Citation

  • Jiayan Li & Ziyang Dong & Yang Chen & Zhanhui Yang & Xinen Yan & Meng Wang & Chenyang Li & Changgui Zhao, 2024. "N-Heterocyclic carbene-catalyzed enantioselective synthesis of planar-chiral cyclophanes via dynamic kinetic resolution," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46376-8
    DOI: 10.1038/s41467-024-46376-8
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-46376-8
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-024-46376-8?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. Matthew N. Hopkinson & Christian Richter & Michael Schedler & Frank Glorius, 2014. "An overview of N-heterocyclic carbenes," Nature, Nature, vol. 510(7506), pages 485-496, June.
    2. Jia-Lei Yan & Rakesh Maiti & Shi-Chao Ren & Weiyi Tian & Tingting Li & Jun Xu & Bivas Mondal & Zhichao Jin & Yonggui Robin Chi, 2022. "Carbene-catalyzed atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    Full references (including those not matched with items on IDEAS)

    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. Lei Zhang & Zhe Chen & Zhenpeng Liu & Jun Bu & Wenxiu Ma & Chen Yan & Rui Bai & Jin Lin & Qiuyu Zhang & Junzhi Liu & Tao Wang & Jian Zhang, 2021. "Efficient electrocatalytic acetylene semihydrogenation by electron–rich metal sites in N–heterocyclic carbene metal complexes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    2. Aliah El Astal-Quirós & Valentina Carrarini & Francesca Zarotti & Atiq Ur Rahman & Agustí Lledós & Cristina G. Yebra & Ernesto de Jesús & Andrea Reale, 2024. "A Doublet State Palladium(I) N-Heterocyclic Carbene Complex as a Dopant and Stabilizer for Improved Photostability in Organic Solar Cells," Energies, MDPI, vol. 17(15), pages 1-19, August.
    3. Yuxing Cai & Yuxin Zhao & Kai Tang & Hong Zhang & Xueling Mo & Jiean Chen & Yong Huang, 2024. "Amide C–N bonds activation by A new variant of bifunctional N-heterocyclic carbene," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    4. Qingyun Wang & Shuquan Wu & Juan Zou & Xuyang Liang & Chengli Mou & Pengcheng Zheng & Yonggui Robin Chi, 2023. "NHC-catalyzed enantioselective access to β-cyano carboxylic esters via in situ substrate alternation and release," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    5. Xin Li & Yi-Lin Wang & Chan Chen & Yan-Yan Ren & Ying-Feng Han, 2022. "A platform for blue-luminescent carbon-centered radicals," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    6. Xiaochen Wang & Rongxin Yang & Binbing Zhu & Yuxiu Liu & Hongjian Song & Jianyang Dong & Qingmin Wang, 2023. "Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    7. Zi-Jing Zhang & Nicolas Jacob & Shilpa Bhatia & Philipp Boos & Xinran Chen & Joshua C. DeMuth & Antonis M. Messinis & Becky Bongsuiru Jei & João C. A. Oliveira & Aleksa Radović & Michael L. Neidig & , 2024. "Iron-catalyzed stereoselective C–H alkylation for simultaneous construction of C–N axial and C-central chirality," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    8. Hai-Ying Wang & Xin-Han Wang & Bang-An Zhou & Chun-Lin Zhang & Song Ye, 2023. "Ketones from aldehydes via alkyl C(sp3)−H functionalization under photoredox cooperative NHC/palladium catalysis," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    9. Liang Ling & Chenyang Hu & Linhong Long & Xue Zhang & Lixing Zhao & Liu Leo Liu & Hui Chen & Meiming Luo & Xiaoming Zeng, 2023. "Chromium-catalyzed stereodivergent E- and Z-selective alkyne hydrogenation controlled by cyclic (alkyl)(amino)carbene ligands," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    10. Runbo Pei & Wenju Chang & Liancheng He & Tao Wang & Yue Zhao & Yong Liang & Xinping Wang, 2024. "Main-group compounds selectively activate natural gas alkanes under room temperature and atmospheric pressure," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    11. Peng Zhou & Wenchang Li & Jianyong Lan & Tingshun Zhu, 2022. "Electroredox carbene organocatalysis with iodide as promoter," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    12. Zhen Lei & Mizuki Endo & Hitoshi Ube & Takafumi Shiraogawa & Pei Zhao & Koichi Nagata & Xiao-Li Pei & Tomoya Eguchi & Toshiaki Kamachi & Masahiro Ehara & Takeaki Ozawa & Mitsuhiko Shionoya, 2022. "N-Heterocyclic carbene-based C-centered Au(I)-Ag(I) clusters with intense phosphorescence and organelle-selective translocation in cells," Nature Communications, Nature, vol. 13(1), pages 1-9, 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:15:y:2024:i:1:d:10.1038_s41467-024-46376-8. 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.