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The utility of the samarium diiodide promoted C-alkylation of peptides for the introduction of new side chains on peptide strands is dramatically enhanced by the initial oxidative degradation of serine residues in small peptides. In this way, cyclic peptides may also be included in this repertoire as a method for the preparation of peptide libraries.
Attempts were made to promote the carbonyl coupling of cyclohexanone to 4-pyridylthioesters of N-carbamate-protected amino acids with the one electron reducing agent, samarium diiodide. Such reactions proved unsuccessful due to the inability of the ketyl-type radical anion intermediate to be reduced to the corresponding dianion at −78°C. Nevertheless, these results explain our recently published work...
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