Journal article

Ring Expansion of Thiolactams via Imide Intermediates: An Amino Acid Insertion Strategy

Jing Shang, Varsha J Thombare, Carlie L Charron, Uta Wille, Craig A Hutton

Chemistry - A European Journal | WILEY-V C H VERLAG GMBH | Published : 2020


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.