Selective hydroalkoxycarbonylation of enamides to N-acyl amino acid esters: Synthetic applications and theoretical studies

S. Klaus, H. Neumann, H. Jiao, A. Jacobi Von Wangelin, D. Gördes, D. Strübing, S. Hübner, M. Hateley, C. Weckbecker, K. Huthmacher, T. Riermeier, M. Beller

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

N-acyl amino acid esters are easily accessible from enamides by cobalt-catalyzed hydroalkoxycarbonylation in moderate to excellent yield. An important reaction parameter for selective carbonylation is the use of low hydrogen partial pressure, which prevents hydrogenation as a side reaction. The reported method is applicable to various enamides and alcohols. A DFT calculation of the catalytic cycle explains the preferred pathway of this reaction.

Original languageEnglish
Pages (from-to)3685-3700
Number of pages16
JournalJournal of Organometallic Chemistry
Volume689
Issue number23
DOIs
StatePublished - 15 Nov 2004
Externally publishedYes

Keywords

  • Amino acids
  • Cobalt
  • DFT calculations
  • Enamides
  • Homogeneous catalysis
  • Hydroalkoxycarbonylation
  • Hydroesterification

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