Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 14, Pages 2481-2498Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700134
Keywords
amine activation; amino acid; amide; iron; catalysis; carbodiimide; steric hindrance
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Funding
- European Union's Horizon research and innovation programme [657883]
- Research Foundation-Flanders (FWO)
- UAntwerpen (BOF)
- Hercules Foundation
- Innovative Medicines Initiative [115360]
- European Union's Seventh Framework Programme
- EFPIA
- Marie Curie Actions (MSCA) [657883] Funding Source: Marie Curie Actions (MSCA)
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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.
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