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Journal Article
Research Support, Non-U.S. Gov't
Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel-Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles.
Journal of Organic Chemistry 2017 August 19
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.
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