期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 13, 页码 5371-5375出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201916534
关键词
2-amidoacrylates; asymmetric hydrogenation; chiral alpha-amino acids; homogeneous catalysis; nickel
资金
- Shanghai Municipal Education Commission [201701070002E00030]
- National Natural Science Foundation of China [21620102003, 21702134, 21991112, 91856106]
- Science and Technology Commission of Shanghai Municipality [17ZR1415200, 19JC1430100]
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 alpha-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 alpha-amino acids, beta-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.
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