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

An asymmetric smile

The formation of all-carbon quaternary centres is a challenging problem in organic chemistry, with far-reaching implications for functional molecule discovery. Now an inventive solution has been developed, using sulfinamides as traceless linkers for an asymmetric radical Truce–Smiles rearrangement.

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

Access options

Buy this article

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

Fig. 1: The Truce–Smiles reaction for the creation of chiral arene molecules.

References

  1. Liu, Y., Han, S.-J., Liu, W.-B. & Stoltz, B. M. Acc. Chem. Res. 48, 740–751 (2015).

    Article  CAS  Google Scholar 

  2. Holden, C. M. & Greaney, M. F. Chem. Eur. J. 23, 8992–9008 (2017).

    Article  CAS  Google Scholar 

  3. Motherwell, W. B. & Pennell, A. M. K. J. Chem. Soc. Chem. Commun. 877–879 (1991).

  4. Loven, R. & Speckamp, W. N. Tetrahedron Lett. 13, 1567–1570 (1972).

    Article  Google Scholar 

  5. Douglas, J. J., Albright, H., Sevrin, M. J., Cole, K. P. & Stephenson, C. R. J. Angew. Chem. Int. Ed. 54, 14898–14902 (2015).

    Article  CAS  Google Scholar 

  6. Tait, M. et al. Org. Lett. 15, 34–37 (2013).

    Article  CAS  Google Scholar 

  7. Hervieu, C. et al. Nat. Chem. https://doi.org/10.1038/s41557-021-00668-4 (2021).

  8. Kong, W., Casimiro, M., Merino, E. & Nevado, C. J. Am. Chem. Soc. 135, 14480–14483 (2013).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Michael F. Greaney.

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

Whalley, D.M., Greaney, M.F. An asymmetric smile. Nat. Chem. 13, 304–305 (2021). https://doi.org/10.1038/s41557-021-00664-8

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41557-021-00664-8

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