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

Glavač, Danijel; Zheng, Chao; Dokli, Irena; You, Shu-Li; Gredičak, Matija (2017) Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles. Journal of Organic Chemistry, 82 (16). pp. 8752-8760. ISSN 0022-3263

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Abstract

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.

Item Type: Article
Additional Information: This work was supported by the Abbvie-Croatian Science Foundation Young Researcher Grant 2015 and Science and Technology Commission of Shanghai Municipality (16490712200). We are grateful to the Croatian Academy of Sciences and Arts, and to the Chinese Academy of Sciences.
Uncontrolled Keywords: asymmetric catalysis; chiral Bronsted acids; indoles; aza-Friedel-Crafts
Subjects: NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Depositing User: Matija Gredičak
Date Deposited: 03 Dec 2018 09:34
Last Modified: 03 Dec 2018 09:34
URI: http://fulir.irb.hr/id/eprint/4366
DOI: 10.1021/acs.joc.7b01420

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