Ligand-free copper-catalyzed coupling of α-amino acids with N-Boc-2-iodoanilines for the synthesis of enantiopure 3-substituted dihydroquinoxalinones

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Abstract

Abstract We report a room temperature and ligand-free copper-catalyzed coupling of α-amino acid with N-Boc-2-iodoanilines. The initially obtained N-arylated α-amino acids could be subsequently transformed into enantiomerically pure 3-aryl or 3-alkyl-substituted dihydroquinoxalinones via acid-mediated Boc-deprotection/condensation. It is of note that no racemization was observed during the two-step dihydroquinoxalinone synthesis, even when employing racemization-prone arylglycine amino acid starting materials.

Original languageEnglish (US)
Article number45614
Pages (from-to)3179-3182
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - Nov 22 2014

Keywords

  • Amino acids
  • Arylation
  • Catalysis
  • Cross-coupling
  • Heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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