Qu Jiaxin, Yang Tongtong, Zhao Xin, Sun Chentong, Yuan Chunhao, Guo Hongchao, Wang Chang
School of Pharmaceutical Sciences & Institute of Materia Medica, Medical Science and Technology Innovation Center, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan, Shandong 250117, P. R. China.
School of Chemistry and Pharmaceutical Engineering, Shandong First Medical University & Shandong Academy of Medical Sciences, Taian, Shandong 271016, P. R. China.
Org Lett. 2024 Nov 1;26(43):9322-9327. doi: 10.1021/acs.orglett.4c03502. Epub 2024 Oct 24.
The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives with moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction of vinyl epoxides, simultaneously providing a rare oxygen-containing active intermediate in this field. The gram-scale preparation and facile derivatization of the cycloadduct highlight the significant synthetic potential of this strategy.
