Metal-Free N–H/C–H Coupling for Efficient Asymmetric Synthesis of Chiral Dihydroquinoxalinones from Readily Available α-Amino Acids

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6 Citations (Scopus)

Abstract

We have developed a method for the synthesis of dihydroquinoxalinones via intramolecular N–H/C–H coupling using hypervalent iodine. The starting materials were prepared from inexpensive and readily available aniline and amino acid derivatives. Various functional groups were tolerated to give multisubstituted dihydroquinoxalinones in moderate to excellent yields. The chirality of the amino acid was transferred to the desired target compound without a loss of enantiomeric excess. Preliminary mechanistic studies indicated that the reaction proceeds via an ionic mechanism.

Original languageEnglish
Pages (from-to)1067-1070
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number8
DOIs
Publication statusPublished - 2018 Feb 28

Keywords

  • Amino acids
  • C–H functionalization
  • C–N coupling
  • Dihydroquinoxalinones
  • Hypervalent iodine

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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