Charging through the looking glass

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Science  03 Nov 2017:
Vol. 358, Issue 6363, pp. 605-606
DOI: 10.1126/science.358.6363.605-f

Like left and right shoes, chiral molecules can manifest two mirror-image enantiomers. In some cases, hindered rotation is the only barrier to sending one such molecule through the looking glass, but more often the chirality is intrinsic to the bonding framework. As such, it is necessary to break and then remake bonds in order to interconvert the enantiomers. Kim et al. report a striking exception to this paradigm. They prepared a compound in which a monoalkylated carbon atom bridges a quinone ring and a hydroquinone ring. Swapping the oxidation levels of these rings inverts the configuration without carbon bond scission or group migration.

J. Am. Chem. Soc. 10.1021/jacs.7b09176 (2017).

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