Synthesis of Trisubstituted Furans via Copper(I)-Catalyzed Strain-Driving Cycloisomerization/Annulative Fragmentation
Ruyu Xie, Zhiqiang Zhao, Yongxing Zhao, Rui Li, Jinzhong Yao, Maozhong Miao
Abstract
formed furan-fused cyclobutenes via Cu(I)-catalyzed cycloisomerization of readily available allenyl ketones bearing a cyclopropyl moiety are a highly reactive and powerful species, which undergo annulative fragmentation with terminal ynones to afford a wide variety of functional furans in moderate to high yields. This ring-distortion protocol features an unprecedented strain-controlled cycloisomerization/Diels-Alder/retro-Diels-Alder (CDRD) sequence under mild conditions.
Topics & Concepts
CycloisomerizationMoietyChemistryFuranRing strainFragmentation (computing)CatalysisRing (chemistry)StereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryComputer scienceOperating systemCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsSynthetic Organic Chemistry Methods