Aymmetric Aza-Friedel–Crafts Reaction of Isatin-Derived Ketimines with Indoles Catalyzed by a Chiral Phase-Transfer Catalyst
Jing Li, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan
Abstract
A highly enantioselective aza-Friedel–Crafts reaction of 1H-indoles with isatin-derived N-Cbz-ketimines catalyzed by quinine-derived phase-transfer catalysts was developed. A series of chiral 3-aminobisindole compounds containing a tetrasubstituted stereocenter were constructed by this protocol in high yields (82–91%) and moderate to excellent enantioselectivities (46–94% ee).
Topics & Concepts
IsatinStereocenterCatalysisFriedel–Crafts reactionEnantioselective synthesisChemistryIndole testOrganic chemistryPhase (matter)Combinatorial chemistryAsymmetric Synthesis and CatalysisChemical Synthesis and AnalysisAsymmetric Hydrogenation and Catalysis