Nickel-catalyzed asymmetric hydrogenation for the preparation of α-substituted propionic acids

Bowen Li, Zhiling Wang, Yicong Luo, Hanlin Wei, Jianzhong Chen (), Delong Liu and Wanbin Zhang ()
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Bowen Li: Shanghai Jiao Tong University
Zhiling Wang: Shanghai Jiao Tong University
Yicong Luo: Shanghai Jiao Tong University
Hanlin Wei: Shanghai Jiao Tong University
Jianzhong Chen: Shanghai Jiao Tong University
Delong Liu: Shanghai Jiao Tong University
Wanbin Zhang: Shanghai Jiao Tong University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Transition metal-catalyzed asymmetric hydrogenation is one of the most efficient methods for the preparation of chiral α-substituted propionic acids. However, research on this method, employing cleaner earth-abundant metal catalysts, is still insufficient in both academic and industrial contexts. Herein, we report an efficient nickel-catalyzed asymmetric hydrogenation of α-substituted acrylic acids affording the corresponding chiral α-substituted propionic acids with up to 99.4% ee (enantiomeric excess) and 10,000 S/C (substrate/catalyst). In particular, this method can be used to obtain (R)-dihydroartemisinic acid with 99.8:0.2 dr (diastereomeric ratio) and 5000 S/C, which is an essential intermediate for the preparation of the antimalarial drug Artemisinin. The reaction mechanism has been investigated via experiments and DFT (Density Functional Theory) calculations, which indicate that the protonolysis of the C-Ni bond of the key intermediate via an intramolecular proton transfer from the carboxylic acid group of the substrate, is the rate-determining step.

Date: 2024
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DOI: 10.1038/s41467-024-49801-0

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