C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions
Publication type: Journal Article
Publication date: 2019-03-05
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30835123
Organic Chemistry
Abstract
A very simple and highly efficient C2-symmetric tertiary amine-squaramide organocatalyst for asymmetric Michael reactions has been elaborated. In the presence of only 1 mol % of this catalyst, kojic acid derivatives and β-dicarbonyl compounds reacted with nitroolefins, affording the corresponding adducts in a nearly quantitative yield with an enantioselectivity up to 99% ee. The kojic acid-derived adducts could be efficiently produced under "green" conditions (in 96% EtOH or pure water). Moreover, due to the very low solubility in organic solvents, the developed nonsupported catalyst could be readily recovered and reused in catalytic reactions up to 7 times. Utmost availability (one-step synthesis without chromatographic purification), high level of stereoinduction, low efficient loading, and recyclability make it attractive for industrial application in the pharmaceutical industry.
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Total citations:
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Citations from 2024:
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(35.48%)
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GOST
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Kucherenko A. et al. C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions // Journal of Organic Chemistry. 2019. Vol. 84. No. 7. pp. 4304-4311.
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Kucherenko A., Kostenko A. A., Komogortsev A., Lichitsky B., Fedotov M. Yu., Zlotin S. G. C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions // Journal of Organic Chemistry. 2019. Vol. 84. No. 7. pp. 4304-4311.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.9b00252
UR - https://doi.org/10.1021/acs.joc.9b00252
TI - C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions
T2 - Journal of Organic Chemistry
AU - Kucherenko, Alexander
AU - Kostenko, Alexey A
AU - Komogortsev, Andrey
AU - Lichitsky, Boris
AU - Fedotov, Michael Yu
AU - Zlotin, Sergei G
PY - 2019
DA - 2019/03/05
PB - American Chemical Society (ACS)
SP - 4304-4311
IS - 7
VL - 84
PMID - 30835123
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2019_Kucherenko,
author = {Alexander Kucherenko and Alexey A Kostenko and Andrey Komogortsev and Boris Lichitsky and Michael Yu Fedotov and Sergei G Zlotin},
title = {C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.joc.9b00252},
number = {7},
pages = {4304--4311},
doi = {10.1021/acs.joc.9b00252}
}
Cite this
MLA
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Kucherenko, Alexander, et al. “C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions.” Journal of Organic Chemistry, vol. 84, no. 7, Mar. 2019, pp. 4304-4311. https://doi.org/10.1021/acs.joc.9b00252.