Journal of Organic Chemistry, volume 83, issue 15, pages 8193-8207
GaCl3-Mediated “Inverted” Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to Allylic Systems
Publication type: Journal Article
Publication date: 2018-07-02
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
A new process of "inverted" formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes (DACs) to allylic systems to give polyfunctionalized cyclopentanes has been developed. Unlike the classical version of formal [3 + 2]-cycloaddition, a DAC acts in this process as a two-carbon synthon (1,2-zwitterionic reactivity type), while an alkene acts as a three-carbon synthon. Tetramethylethylene, allylbenzenes, homoallylbenzene, terminal and internal aliphatic alkenes, and methylenecyclobutane were successfully used as alkenes. Furthermore, in order to suppress annulation at the aromatic ring in 2-arylcyclopropane-1,1-dicarboxylates and enhance the selectivity of the reaction with the allylic system of alkenes, we suggested a new approach for managing the reactivity of DACs involving substitution at both ortho positions of the aromatic ring. Multinuclear NMR spectroscopy was used to study the structure of the 1,2-zwitterionic gallium complexes generated and their properties and to examine the mechanisms of the occurring reactions.
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Citations by publishers
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Zotova M. A. et al. GaCl3-Mediated “Inverted” Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to Allylic Systems // Journal of Organic Chemistry. 2018. Vol. 83. No. 15. pp. 8193-8207.
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Zotova M. A., Novikov R. G., Shulishov E. V., Tomilov Y. V. GaCl3-Mediated “Inverted” Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to Allylic Systems // Journal of Organic Chemistry. 2018. Vol. 83. No. 15. pp. 8193-8207.
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TY - JOUR
DO - 10.1021/acs.joc.8b00959
UR - https://doi.org/10.1021/acs.joc.8b00959
TI - GaCl3-Mediated “Inverted” Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to Allylic Systems
T2 - Journal of Organic Chemistry
AU - Zotova, Maria A
AU - Novikov, Roman G.
AU - Tomilov, Yury V.
AU - Shulishov, Evgeny V.
PY - 2018
DA - 2018/07/02 00:00:00
PB - American Chemical Society (ACS)
SP - 8193-8207
IS - 15
VL - 83
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2018_Zotova,
author = {Maria A Zotova and Roman G. Novikov and Yury V. Tomilov and Evgeny V. Shulishov},
title = {GaCl3-Mediated “Inverted” Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to Allylic Systems},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.8b00959},
number = {15},
pages = {8193--8207},
doi = {10.1021/acs.joc.8b00959}
}
Cite this
MLA
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Zotova, Maria A., et al. “GaCl3-Mediated “Inverted” Formal [3 + 2]-Cycloaddition of Donor–Acceptor Cyclopropanes to Allylic Systems.” Journal of Organic Chemistry, vol. 83, no. 15, Jul. 2018, pp. 8193-8207. https://doi.org/10.1021/acs.joc.8b00959.