Palladium-Catalyzed Nucleophilic Reaction of Alkylidenecyclopropanes with β,γ-Unsaturated α-Ketoesters: Ligand-Controlled Divergent Synthesis
Xin‐Lian Liu, You‐Ya Zhang, Lin Li, Lu-Qi Tan, Yin-Ai Huang, Ai‐Jun Ma, Jin‐Bao Peng
Abstract
A palladium-catalyzed ligand-controlled selective 1,4-addition and cycloaddition reaction of β,γ-unsaturated α-ketoesters with alkylidenecyclopropanes (ACPs) has been developed. Using ACPs and β,γ-unsaturated α-ketoesters as starting materials, γ-dienyl-α-ketoesters and dihydro-2H-pyrans could be prepared selectively by modulating the ligand. A range of multisubstituted α-ketoesters and dihydro-2H-pyrans were obtained in moderate to excellent yields with excellent regioselectivities.
Topics & Concepts
ChemistryPalladiumLigand (biochemistry)NucleophileCatalysisCycloadditionMedicinal chemistryCombinatorial chemistryOrganic chemistryReceptorBiochemistryCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods