Copper-catalyzed diversified annulations between alpha-diketones and alkynyl alpha-diketones

Copper-catalyzed divergent annulations between alpha-diketones and alkynyl alpha-diketones have been achieved, delivering a series of highly functionalized and biologically important cis-hexahydro-2H-cyclopenta[b]furan (HCPF) and 2-hydroxydihydrofuran-3(2H)-one (HDFO) products with high levels of stereoselectivity under identical conditions. The protocol features the use of earth-abundant copper catalyst, mild conditions, shortening synthetic routes in constructing different molecular frameworks, and reducing the corresponding possible waste production. The substituents of the nucleophilic alpha-diketones play crucial roles in switching the reaction pathways. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.