Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System
Konstantin L Ivanov
1, 2
,
Elena V Villemson
1, 2
,
Stanislav I. Bezzubov
3, 4
,
Alexander G. Majouga
1, 5
,
Mikhail Ya Melnikov
2
,
Ekaterina M Budynina
1, 2
Publication type: Journal Article
Publication date: 2017-08-25
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28799329
Organic Chemistry
Abstract
A convenient low-cost method for regioselective ring-opening of donor-acceptor cyclopropanes with the Zn-AcOH reductive system was developed. The general character of the method was displayed via efficient reduction of a representative series of 2-(het)arylcyclopropane-1,1-diesters as well as donor-acceptor cyclopropanes with other types of electron-withdrawing activating groups. This method opens a rapid access to γ-substituted propyl-1,1-diesters, ketoesters, cyanoesters, cyanoamides, dinitriles, etc., many of which are not readily accessible with alternative methods. The utility of the synthesized compounds was demonstrated by transforming them into valuable acyclic and cyclic compounds (including pharmacologically relevant carbazoles, δ-lactams, and oxindole derivatives).
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Total citations:
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Citations from 2024:
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(21.05%)
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GOST
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Ivanov K. L. et al. Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System // Journal of Organic Chemistry. 2017. Vol. 82. No. 18. pp. 9537-9549.
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Ivanov K. L., Villemson E. V., Latyshev G. V., Bezzubov S. I., Majouga A. G., Melnikov M. Y., Melnikov M. Ya., Budynina E. M. Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System // Journal of Organic Chemistry. 2017. Vol. 82. No. 18. pp. 9537-9549.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.7b01549
UR - https://pubs.acs.org/doi/10.1021/acs.joc.7b01549
TI - Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System
T2 - Journal of Organic Chemistry
AU - Ivanov, Konstantin L
AU - Villemson, Elena V
AU - Latyshev, Gennadij V
AU - Bezzubov, Stanislav I.
AU - Majouga, Alexander G.
AU - Melnikov, Mikhail Y.
AU - Melnikov, Mikhail Ya
AU - Budynina, Ekaterina M
PY - 2017
DA - 2017/08/25
PB - American Chemical Society (ACS)
SP - 9537-9549
IS - 18
VL - 82
PMID - 28799329
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2017_Ivanov,
author = {Konstantin L Ivanov and Elena V Villemson and Gennadij V Latyshev and Stanislav I. Bezzubov and Alexander G. Majouga and Mikhail Y. Melnikov and Mikhail Ya Melnikov and Ekaterina M Budynina},
title = {Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.7b01549},
number = {18},
pages = {9537--9549},
doi = {10.1021/acs.joc.7b01549}
}
Cite this
MLA
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Ivanov, Konstantin L., et al. “Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System.” Journal of Organic Chemistry, vol. 82, no. 18, Aug. 2017, pp. 9537-9549. https://pubs.acs.org/doi/10.1021/acs.joc.7b01549.