volume 82 issue 18 pages 9537-9549

Regioselective Hydrogenolysis of Donor-Acceptor Cyclopropanes with Zn-AcOH Reductive System

Elena V Villemson 1, 2
Mikhail Ya Melnikov 2
Publication typeJournal Article
Publication date2017-08-25
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
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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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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
Cite this
MLA Copy
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.