Application of Chiral Multidentate Ligands in Efficient Asymmetric Hydrogenation

Title:

Application of Chiral Multidentate Ligands in Efficient Asymmetric Hydrogenation

Schedule:

Date: 12 April 2023 (Wed)

Time:  2:30pm-3:30pm (HKT)

Venue:

HOC 412

Speaker:

Professor Xumu ZHANG

Department of Chemistry,

Southern University of Science and Technology

Abstract:

Highly efficient and enantioselective hydrogenation is a key generic technology for green drug synthesis. As early as 1998, Professor Zhang proposed the concept of applying the tridentate ligand to hydrogenation of simple ketones and designed and synthesized the ambox ligand, which showed excellent enantioselectivity in ruthenium-catalyzed asymmetric transfer hydrogenation. In 2016, Zhang and coworkers creatively introduced ferrocene skeleton into the tridentate ligand and designed and synthesized a new f-amphox ligand, which showed ultra-high activity and enantioselectivity (>1,000,000 TON, 99% ee) in the hydrogenation of simple ketones. On this basis of amphox, Zhang and coworkers successively developed chiral tridentate ligands f-amphol, f-ampha and f-amphamide based on ferrocene skeleton, as well as electron-rich Heng-PNP based on rigid skeleton. In 2022, Professor Xumu Zhang proposed the concept of ate catalysis (@ catalysis) and a tetradentate ligand based on the ferrocene skeleton, termed as f-phamidol, was developed based on this concept, which can obtain a TON of up to 13,425,000 in asymmetric hydrogenation of simple ketones. These multidentate ligands have been applied to the green synthesis of many important drugs such as Ezetimibe, Montelukast, Phenylephrine, Nicotine, etc., and have achieved remarkable economic benefits.