Nickel-Catalyzed Asymmetric Hydrogenation of α-Substituted Vinylphosphonates and Diarylvinylphosphine Oxides
Hanlin Wei
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorDr. Hao Chen
Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorCorresponding Author
Dr. Jianzhong Chen
Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
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Prof. Dr. Ilya D. Gridnev
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Prospekt 47, Moscow, 119991 Russian Federation
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Prof. Dr. Wanbin Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorHanlin Wei
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorDr. Hao Chen
Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorCorresponding Author
Dr. Jianzhong Chen
Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Ilya D. Gridnev
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Prospekt 47, Moscow, 119991 Russian Federation
Search for more papers by this authorCorresponding Author
Prof. Dr. Wanbin Zhang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China
Search for more papers by this authorAbstract
Chiral α-substituted ethylphosphonate and ethylphosphine oxide compounds are widely used in drugs, pesticides, and ligands. However, their catalytic asymmetric synthesis is still rare. Of the only asymmetric hydrogenation methods available at present, all cases use rare metal catalysts. Herein, we report an efficient earth-abundant transition-metal nickel catalyzed asymmetric hydrogenation affording the corresponding chiral ethylphosphine products with up to 99 % yield, 96 % ee (enantiomeric excess) (99 % ee, after recrystallization) and 1000 S/C (substrate/catalyst); this is also the first study on the asymmetric hydrogenation of terminal olefins using a nickel catalyst under a hydrogen atmosphere. The catalytic mechanism was investigated via deuterium-labelling experiments and calculations which indicate that the two added hydrogen atoms of the products come from hydrogen gas. Additionally, it is believed that the reaction involves a NiII rather than Ni0 cyclic process based on the weak attractive interactions between the Ni catalyst and terminal olefin substrate.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
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