Nickel-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Imines
Bowen Li
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorDr. Jianzhong Chen
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorDr. Zhenfeng Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorProf. Ilya D. Gridnev
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 9808578 Japan
Search for more papers by this authorCorresponding Author
Prof. Wanbin Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorBowen Li
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorDr. Jianzhong Chen
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorDr. Zhenfeng Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorProf. Ilya D. Gridnev
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 9808578 Japan
Search for more papers by this authorCorresponding Author
Prof. Wanbin Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorGraphical Abstract
The first Ni-catalyzed asymmetric hydrogenation of N-sulfonyl imines using H2 gas as a hydrogen source has been realized with excellent enantioselectivity. The presence of an excess of the nickel salt, with respect to the ligand, promotes the formation of the active Ni catalyst. The reaction features a wide substrate scope, low catalyst loading, and convenient removal of the protecting group.
Abstract
An efficient nickel-catalyzed asymmetric hydrogenation of N-tBu-sulfonyl imines was developed with excellent yields and enantioselectivities using (R,R)-QuinoxP* as a chiral ligand. The use of a much lower catalyst loading (0.0095 mol %, S/C=10500) represents the highest catalytic activity for the Ni-catalyzed asymmetric hydrogenations reported so far. Mechanistic studies suggest that a coordination equilibrium exists between the nickel salt and its complex, and that excess nickel salt promotes the formation of the active Ni-complex, and therefore improved the efficiency of the hydrogenation. The catalytic cycle was also investigated by calculations to determine the origin of the enantioselectivity. An extensive network of numerous weak attractive interactions was found to exist between the catalyst and substrate in the transition state and may also contribute to the high catalytic activity.
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