Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • News & Views
  • Published:

Synthetic methodology

Boron-enabled 1,3-metallate shift towards axially chiral alkenes

Nature Chemistry volume 16, pages 8–9 (2024)Cite this article

Subjects

Tetracoordinate boron molecules are the key intermediates in many organoboron-related chemical transformations. Now, using alkynyl tetracoordinate boron species, a nickel-catalysed asymmetric 1,3-metallate shift towards axial chirality has been developed, giving access to various axially chiral alkenes in high efficiency.

This is a preview of subscription content, access via your institution

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Fig. 1: Asymmetric synthesis based on the metallate shift of tetracoordinate borons.

References

  1. Li, X., Zhang, G. & Song, Q. Chem. Commun. 59, 3812–3820 (2023).

    Article  CAS  Google Scholar 

  2. Hillman, M. E. D. J. Am. Chem. Soc. 84, 4715–4720 (1962).

    Article  CAS  Google Scholar 

  3. Sandford, C. & Aggarwal, V. K. Chem. Commun. 53, 5481–5494 (2017).

    Article  CAS  Google Scholar 

  4. Namirembe, S. & Morken, J. P. Chem. Soc. Rev. 48, 3464–3474 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Stymiest, J. L., Bagutski, V., French, R. M. & Aggarwal, V. K. Nature 456, 778–782 (2008).

    Article  CAS  PubMed  Google Scholar 

  6. Leonori, D. & Aggarwal, V. K. Acc. Chem. Res. 47, 3174–3183 (2014).

    Article  CAS  PubMed  Google Scholar 

  7. Zhang, L. et al. Science 351, 70–74 (2016).

    Article  CAS  PubMed Central  Google Scholar 

  8. Wang, H., Jing, C., Noble, A. & Aggarwal, V. K. Angew. Chem. Int. Edn 59, 16859–16872 (2020).

    Article  CAS  Google Scholar 

  9. Sharma, H. A., Essman, J. Z. & Jacobsen, E. N. Science 374, 752–757 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Ma, X. et al. Nat. Chem. https://doi.org/10.1038/s41557-023-01396-7 (2024).

  11. Ishida, N., Miura, T. & Murakami, M. Chem. Commun. 42, 4381–4383 (2007).

    Article  Google Scholar 

  12. Mori, K., Ohmori, K. & Suzuki, K. Angew. Chem. Int. Edn 48, 5633–5637 (2009).

    Article  CAS  Google Scholar 

  13. Song, H. et al. Angew. Chem. Int. Edn 59, 6576–6580 (2020).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, China

    Li-Qing Ren & Chuan He

Authors
  1. Li-Qing Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chuan He
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chuan He.

Ethics declarations

Competing interests

The authors declare no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ren, LQ., He, C. Boron-enabled 1,3-metallate shift towards axially chiral alkenes. Nat. Chem. 16, 8–9 (2024). https://doi.org/10.1038/s41557-023-01399-4

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41557-023-01399-4

Search

Advanced search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing