Stereoselective synthesis of enamides by Pd-catalyzed hydroamidation of electron deficient terminal alkynes.

Hydroamidation of electron-deficient terminal alkynes by amides in presence of Pd-catalyst has been exploited for the stereoselective synthesis of Z-enamides. The possible intramolecular hydrogen bonding between the amido proton and carbonyl oxygen of ester group provides the extra stability to the Z-isomer of vinyl-palladium complex, which subsequently undergoes protodepalladation and leads to the Z-enamide selectively. This process is found to be mild and operationally simple with broad substrate scope.