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Copper(II)-Catalyzed Enantioselective Aza-Friedel–Crafts Reaction of Indoles with Isatin-Derived <i>N</i>-Boc-Ketimines

Leipeng Xue, Jiaqi Hou, Jiahui Li, Tianxu Yu, Qihang Cai, Shibo Yu, Chao Yao, Yue‐Ming Li

2023The Journal of Organic Chemistry11 citationsDOI

Abstract

The copper(II)-catalyzed enantioselective aza-Friedel–Crafts reaction of indoles with isatin-derived N -Boc-ketimines was developed by using tunable chiral O–N–N tridentate ligands derived from BINOL and proline. In general, the reaction afforded chiral 3-indolyl-3-aminooxindoles under mild conditions in high yields (83–97%) with excellent ee (69–99%).

Topics & Concepts

IsatinEnantioselective synthesisFriedel–Crafts reactionCatalysisChemistryCopperIndole testOrganic chemistryMedicinal chemistryCombinatorial chemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis
Copper(II)-Catalyzed Enantioselective Aza-Friedel–Crafts Reaction of Indoles with Isatin-Derived <i>N</i>-Boc-Ketimines | Litcius