jo5b00378_si_001.pdf (2.97 MB)
Catalytic Chemical Amide Synthesis at Room Temperature: One More Step Toward Peptide Synthesis
journal contribution
posted on 2015-05-01, 00:00 authored by Tharwat Mohy El Dine, William Erb, Yohann Berhault, Jacques Rouden, Jérôme BlanchetAn
efficient method has been developed for direct amide bond synthesis
between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic
acid as a highly active bench-stable catalyst. This catalyst was found
to be very effective at room temperature for a large range of substrates
with slightly higher temperatures required for challenging ones. This
methodology can be applied to aliphatic, α-hydroxyl, aromatic,
and heteroaromatic acids as well as primary, secondary, heterocyclic,
and even functionalized amines. Notably, N-Boc-protected
amino acids were successfully coupled in good yields with very little
racemization. An example of catalytic dipeptide synthesis is reported.