C–C Bond Cleavage-Induced C- to N‑Acyl Transfer for Synthesis of Amides

A new approach for the preparation of amides was developed using C–C bond cleavage that initiates C- to N-acyl transfer, employing activated ketones as acylation reagents and amine nucleophiles. The reaction was operational under the coupling reagent system that is commonly utilized for peptide bond...

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Bibliographic Details
Published in:Organic letters 2024-05, Vol.26 (17), p.3646-3651
Main Authors: Lee, Su Eun, Kim, Youngsoo, Lee, Yong Ho, Lim, Hee Nam
Format: Article
Language:English
Subjects:
acylation
amides
cleavage (chemistry)
Lewis bases
peptides
Citations: Items that this one cites
Online Access:Get full text
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Summary:A new approach for the preparation of amides was developed using C–C bond cleavage that initiates C- to N-acyl transfer, employing activated ketones as acylation reagents and amine nucleophiles. The reaction was operational under the coupling reagent system that is commonly utilized for peptide bond formations. The method enables practical preparation of amides using linear and cyclic ketone substrates under mild conditions.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01154