Construction of cyclopentane-fused coumarins via DBU-catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes

Huawei Lin; Huimin Yang; Qi Gong; Shan Luo; Jing Gu; Xiaoqun Cao; Biming Mao; Yanqing Ge; Chunhao Yuan

doi:10.1039/d1ra03387e

Construction of cyclopentane-fused coumarins via DBU-catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes

RSC Adv. 2021 Jun 4;11(33):20118-20122. doi: 10.1039/d1ra03387e. eCollection 2021 Jun 3.

Authors

Huawei Lin¹, Huimin Yang¹, Qi Gong¹, Shan Luo¹, Jing Gu¹, Xiaoqun Cao¹, Biming Mao², Yanqing Ge¹, Chunhao Yuan¹

Affiliations

¹ School of Chemistry and Pharmaceutical Engineering, Shandong First Medical University, Shandong Academy of Medical Sciences Taian 271016 Shandong P. R. China yuanchunhao2017@163.com geyanqing2016@126.com.
² Institute of Materia Medica, Shandong First Medical University, Shandong Academy of Medical Sciences Jinan 250117 Shandong P. R. China maobiming@sdfmu.edu.cn.

Abstract

The metal-free DBU catalyzed [3+2] cycloaddition of 3-homoacyl coumarins with cyclic 1-azadienes proceeded smoothly to furnish the corresponding highly functionalized cyclopentane-fused coumarins with excellent diastereoselectivity and complete chemoselectivity and in good yields under mild conditions.