Intramolecular [3 + 2]-Cycloaddition Reaction of Push−Pull Dipoles Across Heteroaromatic π-Systems

Abstract

[reaction: see text] Push-pull dipoles generated from the Rh(II)-catalyzed reaction of diazo imides containing tethered heteroaromatic rings undergo successful [3 + 2]-cycloaddition across the 2,3-pi-bond to provide novel pentacyclic compounds in good to excellent yields in a stereocontrolled fashion. The facility of the cycloaddition is critically dependent on conformational factors in the transition state.