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

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Copper
Ligands
Amino Acids
Condensation
Temperature
Acids
2-iodobenzenamine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Ligand-free copper-catalyzed coupling of α-amino acids with N-Boc-2-iodoanilines for the synthesis of enantiopure 3-substituted dihydroquinoxalinones",
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.",
keywords = "Amino acids, Arylation, Catalysis, Cross-coupling, Heterocycles",
author = "Sheng Luo and {De Brabander}, {Jef K.}",
year = "2014",
month = "11",
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doi = "10.1016/j.tetlet.2014.12.090",
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pages = "3179--3182",
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T1 - Ligand-free copper-catalyzed coupling of α-amino acids with N-Boc-2-iodoanilines for the synthesis of enantiopure 3-substituted dihydroquinoxalinones

AU - Luo, Sheng

AU - De Brabander, Jef K.

PY - 2014/11/22

Y1 - 2014/11/22

N2 - 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.

AB - 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.

KW - Amino acids

KW - Arylation

KW - Catalysis

KW - Cross-coupling

KW - Heterocycles

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DO - 10.1016/j.tetlet.2014.12.090

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EP - 3182

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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