Switchable Skeletal Rearrangement of Hexahydro-4H-indol-4-ones: Divergent Synthesis of Dihydroxy-4H-cyclopenta[b]pyridin-4-ones and 8-Alkenyl Oxepane-2,6-diones
化学
分子内力
化学选择性
立体化学
重排反应
重排
组合化学
药物化学
有机化学
催化作用
作者
Z. W. Zhang,Haifeng Sun,Mingshuai Zhang,Siyu Song,Min Peng,Wenwen Dai,Yongchao Wang,Fuchao Yu
出处
期刊:Organic Letters [American Chemical Society] 日期:2024-05-14
An unprecedented base-controlled selective skeletal rearrangement reaction of hexahydro-4H-indol-4-ones has been developed. In this protocol, highly functionalized dihydroxy-4H-cyclopenta[b]pyridin-4-ones and 8-alkenyl oxepane-2,6-diones were prepared with a broad substrate scope and high chemoselectivity in moderate to excellent yields selectively by modulating LiOH and Et3N. In addition, the newly formed 8-alkenyl oxepane-2,6-dione scaffolds could be easily further derivatized to 5-(pyrrol-2-yl)dihydrofuran-2(3H)-ones through a rare intramolecular rearrangement reaction.