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Ring Expansion of Thiolactams via Imide Intermediates: An Amino Acid Insertion Strategy
Author(s) -
Shang Jing,
Thombare Varsha J.,
Charron Carlie L.,
Wille Uta,
Hutton Craig A.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005035
Subject(s) - thioamide , chemistry , amino acid , ring (chemistry) , imide , adduct , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry
The Ag I ‐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.