Chiral Phosphoric Acid-Catalyzed C6 Functionalization of 2,3-Disubstituted Indoles for Synthesis of Heterotriarylmethanes
Wen‐Jun Huang, Yaya Ma, Lixia Liu, Bo Wu, Guo‐Fang Jiang, Yong‐Gui Zhou
Abstract
The direct regio- and enantioselective C6 functionalization of 2,3-disubstituted indoles with azadienes has been developed using chiral phosphoric acid as catalyst, providing a convenient approach to synthesize the optically active heterotriarylmethanes with excellent yields, broad substrate scope, and up to 98% ee. Mechanistic studies revealed that N-alkylation of 2,3-disubstituted indoles with azadienes would be reversible, and enantioselective C6 functionalization could be enabled.
Topics & Concepts
Enantioselective synthesisSurface modificationChemistryPhosphoric acidCatalysisSubstrate (aquarium)Combinatorial chemistryAlkylationOptically activeOrganocatalysisOrganic chemistryPhysical chemistryOceanographyGeologyAsymmetric Synthesis and CatalysisSynthesis of Indole DerivativesCatalytic C–H Functionalization Methods