Synthesis of amide bonds is an important issue in organic chemistry, but is often overlooked as a contemporary challenge. Existing methods are reaching their limits and new chemical approaches are being developed. The silver promoted coupling reaction of thioamides with protected amino acids, recently reported in our group, leads to imide formation without epimerisation. This system was shown to be general for various N-protected amino acids and peptides, including preparation of the pentapeptide thymopentin.<br/><br/>However, the hydrolysis of the imide is not always regioselective and occasionally results in undesired bond cleavage, leading us to investigate alternative solutions. Initial studies of series of thioamides bearing a pendant nucleophile show promising results and suggest a general method for directed self-cleavage via intramolecular extrusion of a benzofuranone, forming the desired amide.

New method for selective imide bond cleavage

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.