Access to Chiral Polycyclic 1,4-Dihydropyridines via Organocatalytic Formal [3 + 3] Annulation of 2-(1-Alkynyl)-2-alken-1-ones with 3-Aminobenzofurans
Zhanhuan Li, Hongwei Zhou, Jianfeng Xu
Abstract
A rational designed tandem reaction of 2-(1-alkynyl)-2-alken-1-ones with 3-aminobenzofurans enabled by a chiral bifunctional catalyst is described, affording biologically significant polycyclic 1,4-dihydropyridines in moderate to good yields (43-82%) with good to excellent enantioselectivities (83-99%). This formal [3 + 3] annulation reaction reveals good practicality when conducted on a gram scale, and the cycloadduct has the capability for further elaborations.
Topics & Concepts
AnnulationChemistryBifunctionalTandemCatalysisCombinatorial chemistryFormal synthesisEnantioselective synthesisStereochemistryOrganic chemistryMaterials scienceComposite materialCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms