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Highly Enantioselective Friedel−Crafts Reaction of Aromatic Amines with Ethyl Glyoxylate Catalyzed by Chiral Titanium(IV) Complexes:  Practical Synthesis of Aminomandelic Acid Derivatives

Тип публикацииJournal Article
Дата публикации2003-12-12
scimago Q2
wos Q1
БС1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
Organic Chemistry
Краткое описание
The asymmetric Friedel-Crafts reaction of a variety of N,N-dialkylanilines with ethyl glyoxylate has been achieved by the catalysis of titanium complexes of BINOL derivatives to give corresponding ethyl esters of p-N,N-dialkylaminomandelic acids in high yields (85-99%) and good to excellent enantioselectivities (80-96.6% ee) under the optimized reaction conditions, which has added a new catalyst for this class of reactions. The reaction could also be carried out at a reduced catalyst loading (1 mol %) in gram scale, which provided a practical synthesis of enantiopure aminomandelic acid derivatives.
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ГОСТ |
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Yuan Yu. et al. Highly Enantioselective Friedel−Crafts Reaction of Aromatic Amines with Ethyl Glyoxylate Catalyzed by Chiral Titanium(IV) Complexes: Practical Synthesis of Aminomandelic Acid Derivatives // Journal of Organic Chemistry. 2003. Vol. 69. No. 1. pp. 146-149.
ГОСТ со всеми авторами (до 50) Скопировать
Yuan Yu., Wang X., Li X., Ding K. Highly Enantioselective Friedel−Crafts Reaction of Aromatic Amines with Ethyl Glyoxylate Catalyzed by Chiral Titanium(IV) Complexes: Practical Synthesis of Aminomandelic Acid Derivatives // Journal of Organic Chemistry. 2003. Vol. 69. No. 1. pp. 146-149.
RIS |
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TY - JOUR
DO - 10.1021/jo034992d
UR - https://doi.org/10.1021/jo034992d
TI - Highly Enantioselective Friedel−Crafts Reaction of Aromatic Amines with Ethyl Glyoxylate Catalyzed by Chiral Titanium(IV) Complexes: Practical Synthesis of Aminomandelic Acid Derivatives
T2 - Journal of Organic Chemistry
AU - Yuan, Yu
AU - Wang, Xingwang
AU - Li, Xin
AU - Ding, Kuiling
PY - 2003
DA - 2003/12/12
PB - American Chemical Society (ACS)
SP - 146-149
IS - 1
VL - 69
PMID - 14703390
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
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BibTex (до 50 авторов) Скопировать
@article{2003_Yuan,
author = {Yu Yuan and Xingwang Wang and Xin Li and Kuiling Ding},
title = {Highly Enantioselective Friedel−Crafts Reaction of Aromatic Amines with Ethyl Glyoxylate Catalyzed by Chiral Titanium(IV) Complexes: Practical Synthesis of Aminomandelic Acid Derivatives},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {69},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/jo034992d},
number = {1},
pages = {146--149},
doi = {10.1021/jo034992d}
}
MLA
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Yuan, Yu., et al. “Highly Enantioselective Friedel−Crafts Reaction of Aromatic Amines with Ethyl Glyoxylate Catalyzed by Chiral Titanium(IV) Complexes: Practical Synthesis of Aminomandelic Acid Derivatives.” Journal of Organic Chemistry, vol. 69, no. 1, Dec. 2003, pp. 146-149. https://doi.org/10.1021/jo034992d.