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Metal‐Free N–H/C–H Coupling for Efficient Asymmetric Synthesis of Chiral Dihydroquinoxalinones from Readily Available α‐Amino Acids
Author(s) -
Kanyiva Kyalo Stephen,
Horiuchi Masashi,
Shibata Takanori
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800012
Subject(s) - chemistry , hypervalent molecule , chirality (physics) , intramolecular force , aniline , amino acid , enantiomer , enantioselective synthesis , combinatorial chemistry , enantiomeric excess , stereochemistry , organic chemistry , iodine , catalysis , chiral symmetry , biochemistry , physics , quantum mechanics , nambu–jona lasinio model , quark
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.