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

Research output: Contribution to journalArticleResearchpeer-review

17 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1620-1625
Number of pages6
JournalChemistry - A European Journal
Volume27
Issue number5
DOIs
Publication statusPublished - 21 Jan 2021
Externally publishedYes

Keywords

  • acyl transfer
  • imides
  • ring expansion
  • ring insertion
  • thioamides

Cite this