Skip to main content

Thank you for visiting 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.

Organic chemistry

Natural polarity inverted

The concept of umpolung describes the reversal of the naturally occurring electrostatic polarization of chemical groups. It has now been used to make single mirror-image isomers of nitrogen-containing molecules. See Letter p.445

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

Access options

Rent or buy this article

Get just this article for as long as you need it


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

Figure 1: Umpolung for ketones and imines.
Figure 2: Catalytic enantioselective reactions of umpolung imines.


  1. See all news & views


  1. Vitaku, E., Smith, D. T. & Njardarson, J. T. J. Med. Chem. 57, 10257–10274 (2014).

    Article  CAS  Google Scholar 

  2. Wu, Y., Hu, L. & Deng, L. Nature 523, 445–450 (2015).

    Article  ADS  CAS  Google Scholar 

  3. Seebach, D. Angew. Chem. Int. Ed. 18, 239–258 (1979).

    Article  Google Scholar 

  4. Denmark, S. E. & Wilson, T. W. Nature Chem. 2, 937–943 (2010).

    Article  ADS  CAS  Google Scholar 

  5. Flanigan, D. M., Romanov-Michailidis, F., White, N. A. & Rovis, T. Chem. Rev. (2015).

  6. Brehme, R., Enders, D., Fernandez, R. & Lassaletta, J. M. Eur. J. Org. Chem. 2007, 5629–5660 (2007).

    Article  Google Scholar 

  7. Han, J., Sorochinsky, A. E., Ono, T. & Soloshonok, V. A. Curr. Org. Synth. 8, 281–294 (2011).

    Article  CAS  Google Scholar 

  8. Wu, Y. & Deng, L. J. Am. Chem. Soc. 134, 14334–14337 (2012).

    Article  CAS  Google Scholar 

  9. Xiao, X., Xie, Y., Su, C. Liu, M. & Shi, Y. J. Am. Chem. Soc. 133, 12914–12917 (2011)

    Article  CAS  Google Scholar 

  10. Matsumoto, M., Harada, M., Yamashita, Y. & Kobayashi, S. Chem. Commun. 50, 13041–13044 (2014).

    Article  CAS  Google Scholar 

  11. Liu, X., Gao, A., Ding, L., Xu, J. & Zhao, B. Org. Lett. 16, 2118–2121 (2014).

    Article  CAS  Google Scholar 

  12. Ogle, J. W., Zhang, J., Reibenspies, J. H., Abboud, K. A. & Miller, S. A. Org. Lett. 10, 3677–3680 (2008).

    Article  CAS  Google Scholar 

  13. Kim, H. et al. J. Am. Chem. Soc. 130, 12184–12191 (2008).

    Article  CAS  Google Scholar 

  14. Zhu, Y. & Buchwald, S. L. J. Am. Chem. Soc. 136, 4500–4503 (2014).

    Article  CAS  Google Scholar 

  15. Shirakawa, S. & Maruoka, K. Angew. Chem. Int. Ed. 52, 4312–4348 (2013).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to Tomislav Rovis.

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Romanov-Michailidis, F., Rovis, T. Natural polarity inverted. Nature 523, 417–418 (2015).

Download citation

  • Published:

  • Issue Date:

  • DOI:

This article is cited by


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