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.
[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.
Riber
Ditte
D
Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
Skrydstrup
Troels
T
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
D000577:Amides; D000596:Amino Acids; D004952:Esters; D005609:Free Radicals; D007454:Iodides; D009589:Nitrogen Oxides; C015388:nitrones; D012493:Samarium; C409809:samarium diiodide