3 years ago

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

Takanori Shibata, Kyalo Stephen Kanyiva, Masashi Horiuchi
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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201800012

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