Copper-Catalyzed Annulation of <i>O</i>-Acyl Oximes with Cyclic 1,3-Diones for the Synthesis of 7,8-Dihydroindolizin-5(6<i>H</i>)-ones and Cyclohexanone-Fused Furans
Hai‐Tao Yang, Su-Qing Zhou, Danmei Chen, Zi-Jun Hu, Xiao-Qi Qiang, Xiaoqing Song, Sheng Tan, Weihua Jiang, Yongqiang Sun, Chun‐Bao Miao
Abstract
A copper-catalyzed annulation of O -acyl oximes with cyclic 1,3-diones has been developed for the concise synthesis of 7,8-dihydroindolizin-5(6 H )-ones and cyclohexanone-fused furans through the substituent-controlled selective radical coupling process. 2-Alkyl cyclic 1,3-diones undergo C–C radical coupling, while 2-unsubstituted cyclic 1,3-diones undergo C–O radical coupling.
Topics & Concepts
ChemistryAnnulationCyclohexanoneCatalysisSubstituentMedicinal chemistryCopperOximeAlkylOrganic chemistryStereochemistryCyclopropane Reaction MechanismsSynthesis and Characterization of PyrrolesCatalytic C–H Functionalization Methods