Copper-catalyzed multicomponent assembly of γ-butenolides via the interception of carbonyl ylides with iminium ions

Abstract

A Cu(I)-catalyzed three-component reaction of cyclopropenes, enamines and aldehydes has been realized. This reaction proceeds via the interception of carbonyl oxonium ylide intermediates with α, β-unsaturated iminium ions that are in situ generated from enamines and aldehydes under the catalysis of Cu(MeCN)₄PF₆, leading to the desired γ-butenolide derivatives in good yields and with moderate diastereoselectivities. Access to these derivatives with tethered ketone and alkynal groups will expand the structural diversity of multi-substituted butenolides.