Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Enantioselective Palladium(II)-Catalyzed Intramolecular Aminoarylation of Alkenes by Dual N−H and Aryl C−H Bond Cleavage

Enantioselective Palladium(II)-Catalyzed Intramolecular Aminoarylation of Alkenes by Dual N−H and Aryl C−H Bond Cleavage
Pinhong Chen, Guosheng Liu, Wen Zhang
An asymmetric palladium-catalyzed intramolecular oxidative aminoarylation of alkenes has been developed with quinoline–oxazoline chiral ligands and Ag2CO3 as the oxidant. Various indolines containing a quaternary stereogenic center were synthesized in high yield with excellent enantioselectivity. Preliminary mechanistic studies suggest that the addition of a catalytic amount of phenylglyoxylic acid significantly accelerates the reaction and slightly enhances the enantioselectivity. A neighborhood action group: In an asymmetric palladium-catalyzed intramolecular oxidative aminoarylation of alkenes in the presence of a quinolone–oxazoline chiral ligand and Ag2CO3 as the oxidant, the amide N−H bond of the substrate and a neighboring aryl C−H bond were both activated to react with the alkene (see scheme). Various indolines with a quaternary stereogenic center were synthesized in high yield with excellent enantioselectivity.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700889

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