Efficient enantioselective synthesis of trisubstituted γ-lactam <i>via</i> the Michael addition reaction of 2,3-dioxopyrrolidine with indole in aqueous media
John Kamanda Mansaray, Yekai Huang, Kuiliang Li, Xiang Sun, Zhenggen Zha, Zhiyong Wang
Abstract
An efficient enantioselective Michael addition reaction of 2,3-dioxopyrrolidine with indole in aqueous media was developed by virtue of a chiral copper complex. This reaction features air tolerance, a broad substrate scope and mild reaction conditions. Furthermore, a gram-scale synthesis was conducted to afford the corresponding products with a high yield and excellent enantioselectivity. Moreover, the proposed mechanism was supported by control experiments, XPS investigation and DFT calculations.
Topics & Concepts
Enantioselective synthesisChemistryAqueous mediumMichael reactionIndole testSubstrate (aquarium)Combinatorial chemistryYield (engineering)Aqueous solutionOrganic chemistryCatalysisMetallurgyGeologyOceanographyMaterials scienceAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis