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Ring Expansion of Thiolactams via Imide Intermediates: An Amino Acid Insertion Strategy |
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| Authors: | Dr Jing Shang Dr Varsha J Thombare Dr Carlie L Charron Prof Uta Wille Prof Craig A Hutton |
| Institution: | 1. School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Vic 3010 Australia
These authors contributed equally to this work.;2. School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Vic 3010 Australia |
| 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. |
| Keywords: | acyl transfer imides ring expansion ring insertion thioamides |