Organic Chemistry

A switch in time saves ligand

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Science  31 Jul 2020:
Vol. 369, Issue 6503, pp. 520
DOI: 10.1126/science.369.6503.520-b

Isolating just one of two mirror-image products, or enantiomers, is essential in pharmaceutical synthesis. Often distinct enantiomeric ligands must be appended to a catalyst to steer the reaction one way or the other. Tu et al. report an intriguing case in which a single catalyst produces either product enantiomer, depending on reaction time. An iridium-catalyzed allylation of hydroxyisoquinolines yields one product within 10 minutes via kinetic resolution of the allyl precursors. Over 10 more hours, this initial product comes apart via a catalyzed reaction with the solvent, whereas its enantiomer steadily builds up and stays intact.

Nat. Chem. 10.1038/s41557-020-0489-1 (2020).

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