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.

Details

Title
Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines
Author
Chen, Jianzhong 1 ; Zhang, Zhenfeng 1 ; Bowen, Li 1 ; Li, Feilong 2 ; Wang, Yulin 2 ; Zhao, Min 2 ; Gridnev, Ilya D 3   VIAFID ORCID Logo  ; Imamoto, Tsuneo 4 ; Zhang, Wanbin 1   VIAFID ORCID Logo 

1  Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, China 
2  School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, China 
3  Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki 3-6, Aoba-ku, Sendai, Japan 
4  Department of Chemistry, Graduate School of Science, Chiba University, Chiba, Japan 
Pages
1-10
Publication year
2018
Publication date
Nov 2018
Publisher
Nature Publishing Group
e-ISSN
20411723
Source type
Scholarly Journal
Language of publication
English
DOI
https://doi.org/10.1038/s41467-018-07462-w
ProQuest document ID
2138606074
Copyright
© 2018. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.