The Michael reaction is widely considered one of the most powerful C–C bond-forming transformations. Enolates of ketones and esters have been extensively utilized as carbon nucleophiles in Michael reactions. However, there have been few reports demonstrating the utility of intramolecular Michael additions of aldehyde enolates to α,β-unsaturated carbonyl compounds for the stereoselective synthesis of carbocyclic compounds. This is mainly due to the high reactivity of the formyl group under either basic or acidic reaction conditions required for the direct generation of aldehyde enolates. Herein, we report intramolecular Michael reactions of aliphatic aldehyde enolates generated by imidazolium carbenes for the synthesis of cyclopentane aldehydes.