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Nickel‐Catalyzed Asymmetric Hydrogenation of 2‐Amidoacrylates
Author(s) -
Hu Yawen,
Chen Jianzhong,
Li Bowen,
Zhang Zhenfeng,
Gridnev Ilya D.,
Zhang Wanbin
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201916534
Subject(s) - catalysis , asymmetric hydrogenation , chemistry , nickel , ligand (biochemistry) , combinatorial chemistry , deuterium , enantioselective synthesis , amino acid , organic chemistry , biochemistry , physics , receptor , quantum mechanics
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.