Ligand-free copper-catalyzed coupling of α-amino acids with N-Boc-2-iodoanilines for the synthesis of enantiopure 3-substituted dihydroquinoxalinones
2015
Luo, Sheng | De Brabander, Jef K.
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.
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