Asymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes
Publication type: Journal Article
Publication date: 2005-11-25
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
16388620
Organic Chemistry
Abstract
A novel asymmetric Friedel−Crafts alkylation of indoles with nitroalkenes catalyzed by Zn(II)−bisoxazoline complexes has been developed. The nitroalkylated indoles are synthesized in excellent yields and high enantioselectivities (up to 90% ee). The effects of ligand structure, metal salt, and solvent on the reaction are discussed. The substrates of the reaction can be aromatic, heteroaromatic, and even aliphatic nitroalkenes. The high reactivity and selectivity of the reaction are presumptively attributed to the activation and asymmetric induction of chiral Lewis acids coordinated by nitroalkene substrates through a 1,3-metal bonding model.
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203
Total citations:
203
Citations from 2025:
5
(2.46%)
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GOST
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Jia Y. et al. Asymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes // Journal of Organic Chemistry. 2005. Vol. 71. No. 1. pp. 75-80.
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Jia Y., Zhu S. F., Yang Y., Zhou Q. Asymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes // Journal of Organic Chemistry. 2005. Vol. 71. No. 1. pp. 75-80.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo0516537
UR - https://doi.org/10.1021/jo0516537
TI - Asymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes
T2 - Journal of Organic Chemistry
AU - Jia, Yi-Xia
AU - Zhu, Shuo Fei
AU - Yang, Yun
AU - Zhou, Qilin
PY - 2005
DA - 2005/11/25
PB - American Chemical Society (ACS)
SP - 75-80
IS - 1
VL - 71
PMID - 16388620
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2005_Jia,
author = {Yi-Xia Jia and Shuo Fei Zhu and Yun Yang and Qilin Zhou},
title = {Asymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes},
journal = {Journal of Organic Chemistry},
year = {2005},
volume = {71},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/jo0516537},
number = {1},
pages = {75--80},
doi = {10.1021/jo0516537}
}
Cite this
MLA
Copy
Jia, Yi-Xia, et al. “Asymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes.” Journal of Organic Chemistry, vol. 71, no. 1, Nov. 2005, pp. 75-80. https://doi.org/10.1021/jo0516537.