Research

Asymmetric alkene hydrogenation is responsible for more than 50% of the chiral material in the pharmaceutical industry. State-of-the-art catalysts rely on precious metals such as rhodium, ruthenium and iridium. Our team has pioneered the application of more earth-abundant metals such as iron and cobalt for these transformations. With cobalt, catalysts that are more active and enantioselective compared to precious metals have been discovered. More recent efforts have focused on catalysts differentiated by a single-electron to enable distinct reactivity – most notable in the asymmetric synthesis of sitagliptin. Continuing efforts are focused on the development of new metal precursors to facilitate catalyst discovery by high throughput experimentation and expanding the scope of asymmetric transformations that are currently beyond the reach of precious metals.

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Selected Publications

Mechanistic Investigations of the Asymmetric Hydrogenation of Enamides with Neutral Bis(phosphine) Cobalt Precatalysts
Mendelsohn, L. N.; Pavlovic, L.; Zhong, H.; Friedfeld, M. R.; Shevlin, M.; Hopmann, K. H.; Chirik, P. J.
J. Am. Chem. Soc. 2022, 144, 15764-15778.

Cationic Bis(phosphine) Cobalt(I) Arene Complexes as Precatalysts for the Asymmetric Synthesis of Sitagliptin
MacNeil, C. S.; Zhong, H.; Pabst, T. P.; Shevlin, M.; Chirik, P. J.
ACS Catal. 2022, 12, 4680–4687.

Cobalt-Catalyzed Asymmetric Hydrogenation of alpha, beta-Unsaturated Carboxylic Acids by Homolytic H₂ Cleavage
Zhong, H.; Shevlin, M.; Chirik. P. J.
J. Am. Chem. Soc. 2020, 142, 5272–5281.

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