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 and Wanbin Zhang ()
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Jianzhong Chen: Shanghai Jiao Tong University
Zhenfeng Zhang: Shanghai Jiao Tong University
Bowen Li: Shanghai Jiao Tong University
Feilong Li: East China University of Science and Technology
Yulin Wang: East China University of Science and Technology
Min Zhao: East China University of Science and Technology
Ilya D. Gridnev: Tohoku University, Aramaki 3-6, Aoba-ku
Tsuneo Imamoto: Chiba University
Wanbin Zhang: Shanghai Jiao Tong University

Nature Communications, 2018, vol. 9, issue 1, 1-10

Abstract: 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.

Date: 2018
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DOI: 10.1038/s41467-018-07462-w

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