Nickel-Catalyzed Asymmetric Friedel–Crafts Propargylation of 3-Substituted Indoles with Propargylic Carbonates Bearing an Internal Alkyne Group
Yusuke Miyazaki, Biao Zhou, Hiroaki Tsuji, Motoi Kawatsura
Abstract
The nickel-catalyzed highly enantioselective Friedel-Crafts propargylation of 3-substituted indoles with propargylic carbonates bearing an internal alkyne group was developed. A wide array of the propargylic carbonates as well as 3-substituted indoles can be applicable to the asymmetric nickel catalysis, providing the corresponding chiral C-3 propargylated indolenine derivatives bearing two vicinal chiral centers in up to 89% yield with up to >99% ee and 94:6 dr (24 examples).
Topics & Concepts
AlkyneChemistryCatalysisVicinalYield (engineering)NickelEnantioselective synthesisFriedel–Crafts reactionGroup (periodic table)Bearing (navigation)Organic chemistryCombinatorial chemistryMetallurgyMaterials scienceGeographyCartographyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsAsymmetric Synthesis and Catalysis