Cinchona-alkaloid-derived NN ligands for ruthenium catalyzed asymmetric hydrogenation of ketones

Org Biomol Chem. 2023 Jul 12;21(27):5537-5541. doi: 10.1039/d3ob00371j.

Abstract

A range of cinchona-alkaloid-derived NN ligands bearing N-H were employed for the asymmetric hydrogenation of ketones. By substituting N-H of the ligands, we demonstrated that the N-H moiety was essential for asymmetric hydrogenation and that without the N-H moiety asymmetric hydrogenation could not proceed, based on which a proposed mechanism is discussed. The effectiveness of the optimal ligand was evaluated on various aromatic and α,β-unsaturated ketones, producing the corresponding alcohols with up to 98.8% ee and good yields.