Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates.

Earth-abundant nickel, coordinated with a suitable 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 enantioselectivities (up to 96% ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiencyon a gram scale hydrogenation with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted to chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.

• Publication year

  2020

• Venue

  Angewandte Chemie

• Publication date

  2020-01-20

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/anie.201916534PMID 31958203
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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