22928-63-8Relevant articles and documents
Ring Expansion of Thiolactams via Imide Intermediates: An Amino Acid Insertion Strategy
Shang, Jing,Thombare, Varsha J.,Charron, Carlie L.,Wille, Uta,Hutton, Craig A.
supporting information, p. 1620 - 1625 (2020/12/23)
The AgI-promoted reaction of thiolactams with N-Boc amino acids yields an N-(α-aminoacyl) lactam that can rearrange through an acyl transfer process. Boc-deprotection results in convergence to the ring-expanded adduct, thereby facilitating an overall insertion of an amino acid into the thioamide bond to generate medium-sized heterocycles. Application to the site-specific insertion of amino acids into cyclic peptides is demonstrated.
