Intramolecular Michael Reactions. Addition to the α-Carbon of Ynamides

Article abstract of DOI:10.1021/jo00221a005

A number of substituted cinnamamides were synthesized to determine the feasibility of preparing 4-arylnipecotate derivatives via an intramolecular Michael reaction.With these substrates, β-elimination of the cinnamamide residue was the dominant reaction. 3-Phenylpropynamide substrates, however, underwent an unusual "anti-Michael" addition to the α-carbon of the acetylene to produce pyrrolidinones, whose structures were confirmed by independent synthesis.