Sml2-promoted radical addition of nitrones to αβ-unsaturated amides and esters:: Synthesis of γ-amino acids via a nitrogen equivalent to the ketyl radical

[GRAPHICS] 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.