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

• Published in: Chinese chemical letters 2022-06, Vol.33 (6), p.2997-3002
• Main Authors: Kong, Xiangwen, Yu, Fang, Niu, Shengtong, Gong, Fan, Yang, Shuang, Liu, Jinggong, Luo, Benlong, Fang, Xinqiang
• Format: Article
• Language: English
• Subjects: Atom economy; Copper catalysis; Diversified annulations; Substituents-controlled reactivities; α-Diketones
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2021.11.070

Copper-catalyzed divergent annulations between α-diketones and alkynyl α-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 α-diketones play crucial roles in switching the reaction pathways. [Display omitted] Copper-catalyzed divergent annulations between α-diketones and alkynyl α-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 α-diketones play crucial roles in switching the reaction pathways.