Asymmetric Synthesis of (S)-2-Indolinecarboxylic Acid by Combining Biocatalysis and Homogeneous Catalysis

Ben de Lange, David J. Hyett, Peter J.D. Maas, Daniel Mink, Friso B.J. van Assema, Natascha Sereinig, André H.M. de Vries, Johannes G. de Vries

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Abstract

(S)-2-Indolinecarboxylic acid, an intermediate for ACE inhibitors, was until recently produced by Fischer indole synthesis and classical resolution in seven steps. However, Perkin condensation to form ortho-chlorocinnamic acid, which is converted to (S)-ortho-chlorophenylalanine using the enzyme phenylalanine ammonia lyase prior to copper-catalyzed ring closure thereof delivers the enantiopure product in just three steps.
Original languageEnglish
Pages (from-to)289-292
Number of pages4
JournalChemCatChem
Volume3
Issue number2
DOIs
Publication statusPublished - 2011

Keywords

  • homogeneous catalysis
  • heterocycles
  • copper
  • biocatalysis
  • amino acids

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