title: SmI(2)-promoted radical addition of nitrones to alpha,beta-unsaturated amides and esters: synthesis of gamma-amino acids via a nitrogen equivalent to the ketyl radical.
abstract: [reaction: see text] Alkyl nitrones undergo radical addition reactions to a series of alpha,beta-unsaturated amides and esters when subjected to samarium diiodide via a nitrogen equivalent to a ketyl radical anion. This reaction conveniently provides access to a variety of functionalized gamma-amino acids. The methodology was extended to the asymmetric synthesis of 4-substituted gamma-amino acids, via the nitrone radical addition reaction to acrylates/amides possessing a chiral auxiliary.
authors.affiliation: Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
authors.forename: Ditte
authors.initials: D
authors.lastname: Riber
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry; D012493:Samarium / Q000737:chemistry
chemical_list: D000577:Amides; D000596:Amino Acids; D004952:Esters; D005609:Free Radicals; D007454:Iodides; D009589:Nitrogen Oxides; C015388:nitrones; D012493:Samarium; C409809:samarium diiodide