engleski

Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles

Asymmetric addition of indoles to cyclic α- diaryl-substituted N-acyl imines, which are generated in situ from 3-aryl 3- hydroxyisoindolinones, is described. The transformation proceeds smoothly with a broad range of indoles and isoindolinone alcohols using a SPINOL-derived chiral Brønsted acid catalyst to afford α-tetrasubstituted (3- indolyl)(diaryl)methanamines in excellent yields and enantioselectivities (up to 98% yield, up to >99:1 e.r.). The origin of stereochemical induction is supported by DFT calculations and experimental data.

asymmetric catalysis, chiral Bronsted acid, Friedel-Crafts reaction, quaternary sterecentre

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