The first instance of a molecule in which an oxygen atom is the sole stereocentre has been reported
Scientists have designed and made the first stable chiral compound containing a positively charged oxygen species as the only centre of asymmetry. To accomplish this, they studied oxonium ions, in which an oxygen atom is connected to three other atoms. ‘Such compounds are typically reactive and short-lived, while the oxygen atoms also tend to quickly flip between mirror-image forms,’ says Robert Paton from Colorado State University and the NSF Center for Computer Assisted Synthesis, US, who led the study together with Martin Smith and Jonathan Burton at the University of Oxford in the UK. Paton explains that because of these properties, it hadn’t been possible to isolate oxonium ions as a single enantiomer before. ‘Using a combination of synthetic, analytical and computational studies, we have been able to establish new design rules how to capture a stable chiral oxygen atom,’ he adds.