Hurley visual represents discovery of enantiodivergent decarboxylative asymmetric protonation

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SSPC graduate Dr Cian Kingston and Professor of Synthetic Organic Chemistry at University College Dublin and SSPC Co-Principal Investigator, Patrick Guiry’s research features in The Journal of Organic Chemistry on enantiodivergent decarboxylative asymmetric protonation features with a very unusual explanation represented by hurleys. Source and full text: https://pubs.acs.org/doi/10.1021/acs.joc.8b02478.

Using the Irish sport of hurling as an inspiration for this cover, the racemic starting material interacts with the same catalyst derived from Pd (the hurley), the identical chiral ligand L (the hurling ball), in the presence of two different proton sources (Meldrum’s acid and formic acid). One reaction is hit over the hurling goalpost (H) to the right to afford the (R)-product in 92% ee, whereas the other is hit over the hurling goalpost (H) to the left of afford (S)-product in 945 ee.



 

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