Sml_2-Promoted Radical Addition of Nitrones to α,β-Unsaturated Amides and Esters: Synthesis of γ-Amino Acids via a Nitrogen Equivalent to the Ketyl Radical

摘要

Alkyl nitrones undergo radical addition reactions to a series of α,β-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 γ-amino acids. The methodology was extended to the asymmetric synthesis of 4-substituted γ-amino acids, via the nitrone radical addition reaction to acrylates/amides possessing a chiral auxiliary.