Route to Chiral Tetrahydrofuran Acetals via Pd-Catalyzed Asymmetric Allylic Cycloaddition of Vinyl Epoxides with β-Keto Enol Ethers
Meiqi Li, Yiming Liu, Yong Jian Zhang
Abstract
An efficient method for the synthesis of functionalized chiral tetrahydrofuran (THF) acetals via Pd-catalyzed asymmetric allylic cycloaddition has been developed. With a palladium catalyst coordinated by a chiral phosphine ligand, the protocol is enabled to combine readily available vinyl epoxides and β-keto enol ethers to produce THF acetals bearing three stereocenters in a broad substrate scope with uniformly high levels of enantio- and diastereoselectivity.
Topics & Concepts
ChemistryStereocenterCycloadditionEnolTetrahydrofuranAllylic rearrangementCatalysisPhosphineEnantioselective synthesisOrganic chemistryCombinatorial chemistrySolventCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisOxidative Organic Chemistry Reactions