NHC-catalysed [3 + 2]-asymmetric annulation between pyrazolin-4,5-diones and enals: synthesis of novel spirocyclic pyrazolone γ-butyrolactones and computational study of mechanism and stereoselectivity
Marta Gil‐Ordóñez, Alicia Maestro, Pablo Ortega, Pablo G. Jambrina, José M. Andrés
Abstract
Herein we present the first asymmetric synthesis of spiropyrazolone γ-butyrolactones from 1 H -pyrazol-4,5-diones and enals by an NHC-catalysed [3 + 2] annulation. DFT calculations carried out predict the experimental configuration of final adducts.
Topics & Concepts
AnnulationChemistryStereoselectivityPyrazoloneAdductCatalysisEnantioselective synthesisCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms