Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles
Тип публикации: Journal Article
Дата публикации: 2017-08-02
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 5.8
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
28742360
Organic Chemistry
Краткое описание
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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Glavac D. et al. Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles // Journal of Organic Chemistry. 2017. Vol. 82. No. 16. pp. 8752-8760.
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Glavac D., Zheng C., Dokli I., You S., Gredicak M. Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles // Journal of Organic Chemistry. 2017. Vol. 82. No. 16. pp. 8752-8760.
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TY - JOUR
DO - 10.1021/acs.joc.7b01420
UR - https://doi.org/10.1021/acs.joc.7b01420
TI - Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles
T2 - Journal of Organic Chemistry
AU - Glavac, Danijel
AU - Zheng, Chao
AU - Dokli, Irena
AU - You, Shu-Li
AU - Gredicak, Matija
PY - 2017
DA - 2017/08/02
PB - American Chemical Society (ACS)
SP - 8752-8760
IS - 16
VL - 82
PMID - 28742360
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2017_Glavac,
author = {Danijel Glavac and Chao Zheng and Irena Dokli and Shu-Li You and Matija Gredicak},
title = {Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.joc.7b01420},
number = {16},
pages = {8752--8760},
doi = {10.1021/acs.joc.7b01420}
}
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MLA
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Glavac, Danijel, et al. “Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles.” Journal of Organic Chemistry, vol. 82, no. 16, Aug. 2017, pp. 8752-8760. https://doi.org/10.1021/acs.joc.7b01420.
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