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

The gains from breaking symmetry

All-carbon quaternary centres are challenging targets in organic synthesis. Now, the development of a zinc-catalysed desymmetrization method enables the synthesis of chiral alcohols with all-carbon quaternary centres by the selective reduction of symmetrical α,α-disubstituted malonates.

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: Zinc-catalysed desymmetrization reaction of malonic esters.

References

  1. Mikami, K. & Lautens, M. (eds) New Frontiers in Asymmetric Catalysis (Wiley-VCH, 2007).

  2. Todd, M. (ed.) Separation of Enantiomers (Wiley-VCH, 2014).

  3. Zeng, X.-P., Cao, Z.-Y., Wang, Y.-H., Zhou, F. & Zhou, J. Chem. Rev. 116, 7330–7396 (2016).

    Article  CAS  Google Scholar 

  4. Xu, P. & Huang, Z. Nat. Chem. https://doi.org/10.1038/s41557-021-00715-0 (2021).

    Article  PubMed  Google Scholar 

  5. García-Urdiales, E., Alfonso, I. & Gotor, V. Chem. Rev. 105, 313–354 (2005).

    Article  Google Scholar 

  6. Provencher, L. & Jones, J. B. J. Org. Chem. 59, 2729–2732 (1994).

    Article  CAS  Google Scholar 

  7. Mimoun, H., de Saint Laumer, J. Y., Giannini, L., Scopelliti, R. & Floriani, C. J. Am. Chem. Soc. 121, 6158–6166 (1999).

    Article  CAS  Google Scholar 

  8. Trost, B. M., Hung, C.-I. (J.) & Mata, G. Angew. Chem. Int. Ed. 59, 4240–4261 (2020).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Marcin Kwit.

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

Gajewy, J., Kwit, M. The gains from breaking symmetry. Nat. Chem. 13, 623–624 (2021). https://doi.org/10.1038/s41557-021-00731-0

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41557-021-00731-0

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