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  • Title: SmI2 reduced thioesters as synthons of unstable acyl radicals: direct synthesis of potential protease inhibitors via intermolecular radical addition.
    Author: Blakskaer P, Høj B, Riber D, Skrydstrup T.
    Journal: J Am Chem Soc; 2003 Apr 09; 125(14):4030-1. PubMed ID: 12670207.
    Abstract:
    Aromatic alpha-heterosubstituted thioesters were found to undergo radical 1,4-addition reactions to a series of alpha,beta-unsaturated amides and one ester when subjected to the single electron reducing agent, samarium diiodide, at -78 degrees C. These thioesters derived from alpha-amino acids represent a synthetically useful synthon of unstable acyl radicals. This reaction conveniently provides access to gamma-ketoamides and esters in yields up to 90%, structures that are common in various protease inhibitors derived from peptides. Examples with acryloyl and methacryloyl derivatives of alpha-amino acids and dipeptides lead directly to tri- and tetrapeptide mimetics possessing the gamma-ketoamide functionality. No epimerization was observed with the mild conditions used for these reactions.
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