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Organic chemistry

Natural polarity inverted

Nature volume 523, pages 417–418 (2015)Cite this article

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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

The action of biologically active molecules depends on the precise spatial arrangement of atoms that interact with biological targets. More than 95% of drug molecules1 contain nitrogen atoms because they improve the cell permeability and water solubility of the compounds, and strengthen their interactions with biological targets. Methods for the spatially selective assembly of nitrogen-containing molecules are therefore of considerable interest for drug discovery. Moreover, biological targets have a particular chirality (handedness). The ability to synthesize just one chiral form — one enantiomer — of biologically active compounds is thus also of great importance, because only molecules of the correct handedness will fit into their targets, in the same way that right-handed gloves best accommodate right hands. On page 445 of this issue, Deng and colleagues2 report a method that solves both problems by reversing the natural electrostatic polarization of groups called imines.

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

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Authors and Affiliations

  1. Fedor Romanov-Michailidis and Tomislav Rovis are in the Chemistry Department, Colorado State University, Fort Collins, Colorado 80523, USA.,

    Fedor Romanov-Michailidis & Tomislav Rovis

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  1. Fedor Romanov-Michailidis
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  2. Tomislav Rovis
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Correspondence to Tomislav Rovis.

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Romanov-Michailidis, F., Rovis, T. Natural polarity inverted. Nature 523, 417–418 (2015). https://doi.org/10.1038/523417a

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