Synergic effect of hydrogen bonding and dipole repulsion in the ring-closing metathesis of N-homoallyl-2-(hydroxymethyl)acrylamides

Abstract This study reveals that the Ru-catalyzed ring-closing metathesis of N -homoallyl-2-(hydroxymethyl)acrylamides is promoted by substrate-catalyst hydrogen bonding as well as dipole repulsion between the electron-rich side-chain and the carbonyl group, providing clues for designing effective synthetic routes towards 5,6-dihydro-2(1 H )-pyridinones.