Lewis acid-catalyzed reactions of donor–acceptor cyclopropanes with furan derivatives

Abstract

Lewis acid-catalyzed reactions of dialkyl 2-arylcyclopropane-1,1-dicarboxylates with 2,5-dimethylfuran were found to give products of [3+2]-cycloaddition to C(2)–C(3) bond, which contain reactive vinyl ether moiety. These adducts can be further transformed into various products depending on the Lewis acid, the nucleophilicity of aryl group in starting cyclopropane and the ratio of reagents. The vinyl ether moiety can attack the appropriate nucleophilic center in intramolecular or intermolecular mode or can undergo cycloaddition to the second equivalent of donor–acceptor cyclopropane. Alternatively, 2,5-diphenylfuran formed Friedel–Crafts products only when reacted with donor–acceptor cyclopropanes.