Palladium-Catalyzed Hydroalkoxycarbonylation and Hydroxycarbonylation of Cyclopent-3-en-1-ols: Divergent Synthesis of Bridged Cyclic Lactones and β,γ-Unsaturated Carboxylic Acids
Ming Chen, Yang Li, Zheng‐Hui Guan
Abstract
Herein, we report a palladium-catalyzed hydroalkoxycarbonylation and hydroxycarbonylation of cyclopent-3-en-1-ols to form bridged bicyclic lactones and β,γ-unsaturated carboxylic acid. The divergent reactivity of cyclopent-3-en-1-ols is mainly tuned by the palladium catalyst and ligands. The reaction occurs additive-free and has a broad substrate scope. Several valuable synthetic and medical intermediates are accessible through this protocol.
Topics & Concepts
ChemistryPalladiumCatalysisReactivity (psychology)Bicyclic moleculeSubstrate (aquarium)Carboxylic acidMedicinal chemistryStereochemistryOrganic chemistryCombinatorial chemistryMedicineGeologyPathologyOceanographyAlternative medicineAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods