Theoretical study of the mechanism of the N-heterocyclic carbene-catalyzed cyclotetramerization of acrylates.
A theoretical study of the N-heterocyclic carbene (NHC)-catalyzed cyclotetramerization of acrylates forming trisubstituted cyclopentenones indicates a mechanism through a key deoxy-Breslow intermediate generated from one molecule of NHC and two molecules of methyl acrylate (MA). Pathways involving different proton-transfer (α or β) and the role of a tert-butoxide ( (t) BuO(-)) group were investigated.