Riber Ditte, Skrydstrup Troels
Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
Org Lett. 2003 Jan 23;5(2):229-31. doi: 10.1021/ol027386y.
[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.
[反应：见正文] 当烷基硝酮与二碘化钐作用时，通过与酮基自由基阴离子相当的氮，它们会与一系列α,β-不饱和酰胺和酯发生自由基加成反应。该反应方便地提供了获得各种官能化γ-氨基酸的途径。该方法通过硝酮自由基加成反应扩展到了对具有手性助剂的丙烯酸酯/酰胺进行4-取代γ-氨基酸的不对称合成。
