Asymmetric hydrogenation reactions have become vital to the synthesis of molecules important in the pharmaceutical industry. Recently, an efficient asymmetric Ru catalyzed hydrogenation of pyridine-pyrroline tri-substituted alkenes was reported. Nitrogen containing heterocycles are particularly important due to their prevalence in biologically active molecules. Kinetic, spectroscopic, and computational analysis indicated that the addition of H<sub>2</sub> was the rate determining step and that the resting state of the catalyst likely exists off-cycle. Additionally, an unexpected H/D exchange was observed at low temperatures and pressures, where hydrogenation is suppressed. Ultimately, the development of this Ru catalyzed hydrogenation allowed for the synthesis of these important motifs and the subsequent mechanistic investigation highlighted the details of this transformation.

Ru-catalyzed enantioselective hydrogenation of 2-pyridyl substituted alkenes and substrate-mediated H/D exchange

ACS Spring 2022

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