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
Abstract
-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.
Topics & Concepts
ThioamideChemistryAmino acidImideRing (chemistry)AdductStereochemistryCombinatorial chemistryOrganic chemistryBiochemistryChemical Synthesis and AnalysisSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques