Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines

Jianzhong Chen; Zhenfeng Zhang; Bowen Li; Feilong Li; Yulin Wang; Min Zhao; Ilya D Gridnev; Tsuneo Imamoto; Wanbin Zhang

doi:10.1038/s41467-018-07462-w

Pd(OAc)₂-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines

Nat Commun. 2018 Nov 27;9(1):5000. doi: 10.1038/s41467-018-07462-w.

Authors

Jianzhong Chen¹, Zhenfeng Zhang¹, Bowen Li¹, Feilong Li², Yulin Wang², Min Zhao², Ilya D Gridnev³, Tsuneo Imamoto⁴, Wanbin Zhang⁵

Affiliations

¹ Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.
² School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, China.
³ Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki 3-6, Aoba-ku, Sendai, 9808578, Japan.
⁴ Department of Chemistry, Graduate School of Science, Chiba University, Chiba, 263-8522, Japan.
⁵ Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China. wanbin@sjtu.edu.cn.

Abstract

Asymmetric hydrogenation of sterically hindered substrates still constitutes a long-standing challenge in the area of asymmetric catalysis. Herein, an efficient palladium acetate (an inexpensive Pd salt with low toxicity) catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines is realized with high catalytic activities (S/C up to 5000) and excellent enantioselectivities (ee up to 99.9%). Quantum chemical calculations suggest that uniformly high enantioselectivities are observed due to the structurally different S- and R-reaction pathways.

Publication types

Research Support, Non-U.S. Gov't