Silver(I)-Catalyzed Domino Cyclization/Cyclopropanation/Ring-Cleavage/Nucleophilic Substitution Reaction of Enynones with Enamines: Synthesis of 4-(Furan-2-yl)-3,4-dihydro-2<i>H</i>-pyrrol-2-one
Haiyun Peng, Yu Zhang, Yang Zhu, Guisheng Deng
Abstract
We report the synthesis of 4-(furan-2-yl)-3,4-dihydro-2H-pyrrol-2-one derivatives. In this approach, two core structures, the furan ring and 3,4-dihydro-2H-pyrrol-2-one, are constructed via silver(I)-catalyzed cascade cyclization/cyclopropanation/ring-cleavage/nucleophilic substitution reaction of enynones with enamines. A reasonable mechanism has been proposed. This method possesses some advantages such as high chemoselectivity, mild reaction conditions, simple operation, and short reaction time.
Topics & Concepts
ChemistryCyclopropanationFuranChemoselectivityCascade reactionCatalysisMedicinal chemistryRing (chemistry)NucleophileNucleophilic substitutionDominoCleavage (geology)StereochemistryCombinatorial chemistryOrganic chemistryEngineeringFracture (geology)Geotechnical engineeringCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsAsymmetric Synthesis and Catalysis