Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates

Yawen Hu, Jianzhong Chen, Bowen Li, Zhenfeng Zhang, Ilya D. Gridnev, Wanbin Zhang

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5371-5375
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number13
DOIs
Publication statusPublished - 2020 Mar 23

Keywords

  • 2-amidoacrylates
  • asymmetric hydrogenation
  • chiral α-amino acids
  • homogeneous catalysis
  • nickel

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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