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Amine Activation: N ‐Arylamino Acid Amide Synthesis from Isothioureas and Amino Acids
Author(s) -
Zhu YanPing,
Mampuys Pieter,
Sergeyev Sergey,
Ballet Steven,
Maes Bert U. W.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700134
Subject(s) - chemistry , amide , amine gas treating , thioether , amino acid , epimer , catalysis , reagent , enantioselective synthesis , medicinal chemistry , organic chemistry , stereochemistry , biochemistry
N ‐arylamino acid amides have been synthesized via a novel method based on N ‐arylamine activation into isothioureas followed by reaction with amino acids under iron catalysis. The activated N ‐arylamines are easily prepared using a three‐component reaction with commercial reagents, tert ‐butylisocyanide and S ‐phenyl benzenethiosulfonate. The protocol shows a broad functional group compatibility, with respect to side chain functionality of the amino acid (e. g. aliphatic and aromatic OH, (hetero)aromatic NH, amide NH, thioether), and the chiral amino acids do not undergo epimerization. The mechanism of the new amide synthesis has been studied.