DFT calculations were employed to study the asymmetric transfer hydrogenation of ketones catalyzed by rhodium-arene complexes containing hydroxamic acid functionalized amino acid ligands.Three factors were demonstrated to influence the stereoselectivity of the process, namely the energy difference between the metal-ligand binding modes, the energy difference between the intermediate hydrogenated catalyst, and the existence of a stabilizing C-H/p-interaction between the Cp* ligand of the catalyst and the phenyl moiety of the substrate.A technical observation made was that inclusion of dispersion interactions proved to be very important for reproducing the experimentally observed enantioselectivity.

Theoretical study of asymmetric transfer hydrogenation of ketones catalyzed by amino-acid-derived rhodium complexes

244th National Meeting (2012)

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