Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 16, Pages 8752-8760Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01420
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- Abbvie-Croatian Science Foundation
- Science and Technology Commission of Shanghai Municipality [16490712200]
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Asymmetric addition of indoles to cyclic alpha-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 Bronsted acid catalyst to afford alpha-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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