Nickel-Catalyzed β-Carboxylation of Ynamides with Carbon Dioxide

Ryohei Doi, Taichi Okano, Iman Abdullah, Yoshihiro Sato

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

A nickel-catalyzed β-selective hydrocarboxylation of ynamides to give protected dehydro-β-amino acids was developed. The key to exclusive β-selectivity was the use of diethylzinc as a reductant in the presence of a magnesium salt. The reaction was conducted with bis(acetylacetonato)nickel(II) instead of costly and sensitive bis(1,5-cyclooctadiene)nickel(0). In addition, the optimized ligand was inexpensive 1,5-cyclooctadiene. Investigation of the substrate scope revealed that both nitrogen and alkyne substituents have marked effects on the reaction efficiency. We obtained experimental clues that indicated the formation of a vinylzinc intermediate that forms a C-C bond with CO 2 .

Original languageEnglish
Pages (from-to)1048-1052
Number of pages5
JournalSynlett
Volume30
Issue number9
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • carbon dioxide
  • hydrocarboxylation
  • nickel catalysis
  • ynamides
  • β-amino acids

Fingerprint

Dive into the research topics of 'Nickel-Catalyzed β-Carboxylation of Ynamides with Carbon Dioxide'. Together they form a unique fingerprint.

Cite this