Organocatalytic inverse-electron-demand Diels–Alder reaction between 5-alkenyl thiazolones and β,γ-unsaturated carbonyl compounds
Kaixuan Yang, Dongsheng Ji, Haixue Zheng, Yu‐Cheng Gu, Peng‐Fei Xu
Abstract
An inverse-electron-demand oxa-Diels-Alder reaction of 5-alkenyl thiazolones with β,γ-unsaturated carbonyl compounds enabled by quinine thiourea was studied, which allows the enantioselective synthesis of a broad range of highly functionalized pyranthiazoles bearing three continuous stereocenters. This protocol is adaptable to a wide scope of substrates and has great potential for scale-up synthesis and facile transformation.
Topics & Concepts
StereocenterEnantioselective synthesisChemistryThioureaCombinatorial chemistryDiels–Alder reactionOrganic chemistryCatalysisOxidative Organic Chemistry ReactionsCyclopropane Reaction MechanismsAsymmetric Synthesis and Catalysis