Cycloaddition versus amidation in reactions of 2-amino-2-oxoethyl-phenanthrolinium ylides to activated alkynes and alkenes

A comparative study regarding cycloaddition versus amidation reactions of 2-amino-2-oxoethyl-phenanthrolinium ylides to activated alkynes and alkenes is presented. The reaction pathway is different, depending on dipolarophile (with triple or double bond) and ylide structures. The monoenamidation reaction proved to be stereoselective leading to a Z-stereochemistry on the acrylate double bond. The structures of all newly synthesized compounds have been proved by spectral analysis (NMR and IR) and in some cases by X-ray diffraction.