Metal-catalyzed hydrogenations is an important class of organic transformations. These reactions serve as an invaluable access point to a multitude of complex molecules. Research team of Chris Senanayake at Boehringer-Ingelheim designed novel highly efficient catalytic processes for hydrogenation of tetralones and pyridinium salts. Here we present our quantum-chemical studies of the mechanisms of these reactions and the origins of stereoselectivity. We propose involvement of dimers in the mixed-ligand Cu-catalyzed hydrogenation of tetralones and the unusual stereoselectivity control in Ir-catalyzed hydrogenation, where the stereo outcome of final hydride transfer is determined by the preceding protonation.

Computational study of stereoselectivity in Cu and Ir-catalyzed hydrogenations

256th National Meeting (2018)

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