Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates |
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| Authors: | Yawen Hu Dr Jianzhong Chen Bowen Li Dr Zhenfeng Zhang Prof Dr Ilya D Gridnev Prof Dr Wanbin Zhang |
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| Institution: | 1. Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China;2. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 P. R. China;3. Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki 3-6, Aoba-ku, Sendai, 980-8578 Japan |
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| Abstract: | Earth-abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations. |
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| Keywords: | 2-Amidoacrylate Asymmetrische Hydrierung Chirale α-Aminosäuren Homogene Katalyse Nickel |
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