Highly enantioselective δ-protonation and formal [3 + 3] annulation promoted by N-heterocyclic carbene
Mengdie Dong, Xiaoyong Duan, Yanting Li, Binghao Liu, Jing Qi
Abstract
A chiral NHC catalyst reacts with α,β-γ,δ-diunsaturated aldehydes to generate an extended Breslow intermediate. Upon δ-protonation and tautomerization, the resulting α,β-unsaturated acyl azolium undergoes [3 + 3] annulation with enamines to afford various dihydropyridinones.
Topics & Concepts
AnnulationChemistryTautomerProtonationCarbeneEnantioselective synthesisCatalysisMedicinal chemistryStereochemistryOrganic chemistryIonN-Heterocyclic Carbenes in Organic and Inorganic ChemistryAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods