N-Heterocyclic Carbene-Catalyzed Reaction of Chalcone and Cinnamaldehyde To Give 1,3,4-Triphenylcyclopentene Using Organocatalysis To Form a Homoenolate Equivalent

Abstract

In this experiment, students carry out a modern organocatalytic reaction using IMes·HCl and NaOH to catalyze the formation of 1,3,4-triphenylcyclopentene from cinnamaldehyde and chalcone in water. Deprotonation of IMes·HCl with NaOH forms the N-heterocyclic carbene IMes that reacts with cinnamaldehyde to form a homoenolate equivalent of cinnamate, which undergoes a conjugate addition to chalcone followed by an intramolecular aldol reaction to form a cyclopentane. Formation of a β-lactone and decarboxylation leads to 1,3,4-triphenylcyclopentene. This reaction introduces students to both organocatalysis and the use of carbonyl anion and homoenolate equivalents in synthesis. This novel and interesting chemistry was first reported in 2006, and the reaction was modified to be carried out in water under an air atmosphere in 2013. The very nonpolar product is easily purified chromatographically. The aliphatic protons form a somewhat complex pattern due to allylic and homoallylic coupling, but with no overlap, so...