Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles
Publication type: Journal Article
Publication date: 2017-08-02
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28742360
Organic Chemistry
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.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
2
4
6
8
10
|
|
|
Organic and Biomolecular Chemistry
10 publications, 16.13%
|
|
|
Journal of Organic Chemistry
6 publications, 9.68%
|
|
|
Organic Letters
5 publications, 8.06%
|
|
|
Chemical Communications
5 publications, 8.06%
|
|
|
Advanced Synthesis and Catalysis
4 publications, 6.45%
|
|
|
Chemistry - A European Journal
3 publications, 4.84%
|
|
|
RSC Advances
3 publications, 4.84%
|
|
|
Tetrahedron Letters
2 publications, 3.23%
|
|
|
Angewandte Chemie - International Edition
2 publications, 3.23%
|
|
|
Angewandte Chemie
2 publications, 3.23%
|
|
|
Asian Journal of Organic Chemistry
2 publications, 3.23%
|
|
|
European Journal of Organic Chemistry
2 publications, 3.23%
|
|
|
Chemistry - An Asian Journal
2 publications, 3.23%
|
|
|
Chinese Journal of Chemistry
2 publications, 3.23%
|
|
|
Organic Chemistry Frontiers
2 publications, 3.23%
|
|
|
Synthesis
2 publications, 3.23%
|
|
|
Mini-Reviews in Organic Chemistry
1 publication, 1.61%
|
|
|
E3S Web of Conferences
1 publication, 1.61%
|
|
|
Molecules
1 publication, 1.61%
|
|
|
Chem
1 publication, 1.61%
|
|
|
ChemPhotoChem
1 publication, 1.61%
|
|
|
Green Synthesis and Catalysis
1 publication, 1.61%
|
|
|
Chemical Reviews
1 publication, 1.61%
|
|
|
ChemistrySelect
1 publication, 1.61%
|
|
|
2
4
6
8
10
|
Publishers
|
5
10
15
20
25
|
|
|
Wiley
21 publications, 33.87%
|
|
|
Royal Society of Chemistry (RSC)
20 publications, 32.26%
|
|
|
American Chemical Society (ACS)
12 publications, 19.35%
|
|
|
Elsevier
4 publications, 6.45%
|
|
|
Georg Thieme Verlag KG
2 publications, 3.23%
|
|
|
Bentham Science Publishers Ltd.
1 publication, 1.61%
|
|
|
EDP Sciences
1 publication, 1.61%
|
|
|
MDPI
1 publication, 1.61%
|
|
|
5
10
15
20
25
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
62
Total citations:
62
Citations from 2024:
13
(20%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
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.
GOST all authors (up to 50)
Copy
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.
Cite this
RIS
Copy
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 -
Cite this
BibTex (up to 50 authors)
Copy
@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}
}
Cite this
MLA
Copy
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.
Profiles