Journal of Organic Chemistry, volume 86, issue 6, pages 4567-4579
“Cyclopropanation of Cyclopropanes”: GaCl3-Mediated Ionic Cyclopropanation of Donor–Acceptor Cyclopropanes with Diazo Esters as a Route to Tetrasubstituted Activated Cyclopropanes
Publication type: Journal Article
Publication date: 2021-03-04
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
A new ionic cyclopropanation process involving the addition of diazo esters to donor-acceptor cyclopropanes (DAC) activated by GaCl3 has been developed. The reactions occur via 1,2-zwitterionic gallium complexes with elimination of nitrogen in all cases to give 1,1,2,3-tetrasubstituted cyclopropanes as the main products. Also, a number of related processes with the formation of various polysubstituted cyclopropanes, alkenes, and cyclobutanes, including products of multiple diazo ester addition, have been developed. Obtained by the developed method tetrasubstituted cyclopropanes are activated cyclopropanes such as DAC and can be used for further synthesis in this capacity. Their new reaction with benzaldehyde promoted by TiCl4 and involving one of the additional functional groups has been demonstrated, which leads to five-membered lactones. The mechanisms of the occurring processes, as well as the structures and stereochemistry of a rich range of products formed, are discussed in detail.
Top-30
Citations by journals
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Journal of Organic Chemistry
2 publications, 28.57%
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Journal of the American Chemical Society
1 publication, 14.29%
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Organic and Biomolecular Chemistry
1 publication, 14.29%
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Mendeleev Communications
1 publication, 14.29%
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Organic Chemistry Frontiers
1 publication, 14.29%
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Russian Chemical Reviews
1 publication, 14.29%
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Citations by publishers
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American Chemical Society (ACS)
3 publications, 42.86%
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Royal Society of Chemistry (RSC)
2 publications, 28.57%
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Elsevier
1 publication, 14.29%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 14.29%
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- We do not take into account publications without a DOI.
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Borisova I. A. et al. “Cyclopropanation of Cyclopropanes”: GaCl3-Mediated Ionic Cyclopropanation of Donor–Acceptor Cyclopropanes with Diazo Esters as a Route to Tetrasubstituted Activated Cyclopropanes // Journal of Organic Chemistry. 2021. Vol. 86. No. 6. pp. 4567-4579.
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Borisova I. A., Ratova D. M. V., Potapov K. V., Tarasova A. V., Novikov R. G., Tomilov Y. V. “Cyclopropanation of Cyclopropanes”: GaCl3-Mediated Ionic Cyclopropanation of Donor–Acceptor Cyclopropanes with Diazo Esters as a Route to Tetrasubstituted Activated Cyclopropanes // Journal of Organic Chemistry. 2021. Vol. 86. No. 6. pp. 4567-4579.
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TY - JOUR
DO - 10.1021/acs.joc.0c02983
UR - https://doi.org/10.1021/acs.joc.0c02983
TI - “Cyclopropanation of Cyclopropanes”: GaCl3-Mediated Ionic Cyclopropanation of Donor–Acceptor Cyclopropanes with Diazo Esters as a Route to Tetrasubstituted Activated Cyclopropanes
T2 - Journal of Organic Chemistry
AU - Ratova, Daria Maria V
AU - Potapov, Konstantin V
AU - Tarasova, Anna V
AU - Novikov, Roman G.
AU - Borisova, Irina A
AU - Tomilov, Yury V.
PY - 2021
DA - 2021/03/04 00:00:00
PB - American Chemical Society (ACS)
SP - 4567-4579
IS - 6
VL - 86
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2021_Borisova,
author = {Daria Maria V Ratova and Konstantin V Potapov and Anna V Tarasova and Roman G. Novikov and Irina A Borisova and Yury V. Tomilov},
title = {“Cyclopropanation of Cyclopropanes”: GaCl3-Mediated Ionic Cyclopropanation of Donor–Acceptor Cyclopropanes with Diazo Esters as a Route to Tetrasubstituted Activated Cyclopropanes},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.joc.0c02983},
number = {6},
pages = {4567--4579},
doi = {10.1021/acs.joc.0c02983}
}
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Borisova, Irina A., et al. ““Cyclopropanation of Cyclopropanes”: GaCl3-Mediated Ionic Cyclopropanation of Donor–Acceptor Cyclopropanes with Diazo Esters as a Route to Tetrasubstituted Activated Cyclopropanes.” Journal of Organic Chemistry, vol. 86, no. 6, Mar. 2021, pp. 4567-4579. https://doi.org/10.1021/acs.joc.0c02983.
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