Asymmetric Dearomatization of Indole by Palladium/PC‐Phos‐Catalyzed Dynamic Kinetic Transformation
Haoke Chu, Jie Cheng, Junfeng Yang, Yinlong Guo, Junliang Zhang
Abstract
A palladium-catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3-arylindoles with internal alkynes was developed with the use of achiral Xantphos and chiral sulfinamide phosphine ligand (PC-Phos) as the co-ligands. This method could deliver various spiro[indene-1,3'-indole] compounds in good yields (up to 95 % yield) with up to 98 % ee. The salient features of the transformation include the use of readily available substrates, ease of scale-up and the versatile functionalization of the products. The mechanistic experiments gave some insights on active intermediates.
Topics & Concepts
XantphosPalladiumChemistryIndole testCatalysisPhosphineKinetic resolutionCombinatorial chemistryLigand (biochemistry)Yield (engineering)PhosOrganic chemistryEnantioselective synthesisMaterials scienceMetallurgyReceptorBiochemistryCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms