Cut and sew: benzofuran-ring-opening enabled cyclopentenone ring formation
Kai Wang, Chenghao Jiang, Zhenming Zhang, Chunyu Han, Xuewei Wang, Yaping Li, Kaiting Chen, Junfeng Zhao
Abstract
A facile approach to the fully substituted cyclopentenones involving an unprecedented benzofuran-ring-opening is described. The cleavage of a benzofuran endocyclic C2-O bond proceeded smoothly in the absence of any transition metal catalyst or highly reactive organometallic reagent. Such benzofuran-ring-opening is delicately incorporated into an acid-catalyzed cascade process, orchestrating a novel synthetic strategy for complex cyclopentenones with excellent yields and diastereoselectivities.
Topics & Concepts
BenzofuranCyclopentenoneRing (chemistry)ReagentChemistryCatalysisCleavage (geology)Combinatorial chemistryStereochemistryOrganic chemistryMaterials scienceFracture (geology)Composite materialAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions