Highly Enantioselective Synthesis of Pyrroloindolones and Pyrroloquinolinones via an <i>N</i>-Heterocyclic Carbene-Catalyzed Cascade Reaction
Xiaoyong Duan, Zhaohui Tian, Binghao Liu, Tao He, Liangliang Zhao, Mengdie Dong, Pengna Zhang, Jing Qi
Abstract
In this work, the NHC-catalyzed Michael/Mannich/lactamization cascade reaction of enals with either indole-2-carboxaldehyde-derived aldimines or indole-7-carboxaldehyde-derived aldimines is described. This protocol enables the rapid assembly of optically active pyrroloindolones and pyrroloquinolinones derivatives under mild conditions with high yields, excellent enantioselectivities, and a broad substrate scope.
Topics & Concepts
AldimineChemistryEnantioselective synthesisCatalysisCascadeIndole testCarbeneSubstrate (aquarium)Combinatorial chemistryCascade reactionReaction conditionsOrganocatalysisOrganic chemistryChromatographyOceanographyGeologyN-Heterocyclic Carbenes in Organic and Inorganic ChemistryAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods