Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles
Matija Gredičak, Shu-Li You, Irena Dokli, Chao Zheng, Danijel Glavač
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01420

DOI: 10.1021/acs.joc.7b01420

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