The first successful base-promoted isomerization of propargyl amides to chiral ynamides. Applications in ring-closing metathesis of ene-ynamides and tandem RCM of diene-ynamides.

ABSTRACT

[reaction see text] A highly useful sequence of reactions is described here. These reactions consist of the first successful base-induced isomerizations of propargyl amides to chiral ynamides, applications of these novel ynamides in ring-closure metathesis leading to chiral 2-amidodienes useful for Diels-Alder cycloadditions, and the first successful tandem RCM of diene-ynamides.