Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 25, Pages 5692-5700Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300560
Keywords
Amides; Amino acids; Peptides; Organocatalysis; Synethic methods
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Funding
- National Basic Research Program of China [2011CB512007, 2012CB723501]
- National Natural Science Foundation of China (NSFC) [30472074, 30873139]
- Key basic research project of Hebei province of China [12966737D]
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The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65-68 degrees C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings were required and an interesting synergistic catalytic effect between two arylboronic acids was discovered.
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