Journal of Organic Chemistry, volume 86, issue 12, pages 8089-8100
GaCl3-Mediated Cascade [2 + 4]-Cycloaddition/[4 + 2]-Annulation of Donor–Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton
Publication type: Journal Article
Publication date: 2021-05-28
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Structurally important benzobicyclo[3.3.1]nonane derivatives were synthesized by a gallium trichloride mediated reaction of readily available donor-acceptor cyclopropanes (DACs) with 1,3-dienes as a one-pot cascade ionic [2 + 4]-cycloaddition/Friedel-Crafts-type cyclization process. At the first stage, DACs act as sources of formal gallium 1,2-zwitterionic complexes to give 6-benzylcyclohex-3-ene-1,1-dicarboxylates that are converted under certain conditions in the presence of GaCl3 to give benzobicyclo[3.3.1]nonanes in 30-74% yields. The process is tolerant of varying substituents at different positions of the main framework. Further, potentially useful modifications of benzobicyclo[3.3.1]nonane derivatives are demonstrated. 2-Cyclopropylbutadiene reacts with DAC at higher temperature more deeply with cleavage of three-membered rings in both cyclopropane substrates, and twofold alkylation of the Ph-substituent at ortho- and meta-positions, that leads to a 1,2,7,8,9,10-hexahydro-6H-7,10a-methanocycloocta[cd]indene skeleton. Cyclopropane-1,1-diesters containing a bulky substituent in the ester group react with isoprene in a different way to give bicyclic lactones containing a 2-oxabicyclo[2.2.2]octan-3-one moiety.
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- We do not take into account publications without a DOI.
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Belaya M. A. et al. GaCl3-Mediated Cascade [2 + 4]-Cycloaddition/[4 + 2]-Annulation of Donor–Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton // Journal of Organic Chemistry. 2021. Vol. 86. No. 12. pp. 8089-8100.
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Belaya M. A., Knyazev D. A., Borisov D. D., Novikov R. G., Tomilov Y. V. GaCl3-Mediated Cascade [2 + 4]-Cycloaddition/[4 + 2]-Annulation of Donor–Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton // Journal of Organic Chemistry. 2021. Vol. 86. No. 12. pp. 8089-8100.
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TY - JOUR
DO - 10.1021/acs.joc.1c00564
UR - https://doi.org/10.1021/acs.joc.1c00564
TI - GaCl3-Mediated Cascade [2 + 4]-Cycloaddition/[4 + 2]-Annulation of Donor–Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton
T2 - Journal of Organic Chemistry
AU - Belaya, Maria A
AU - Knyazev, Daniil A
AU - Borisov, Denis D
AU - Novikov, Roman G.
AU - Tomilov, Yury V.
PY - 2021
DA - 2021/05/28 00:00:00
PB - American Chemical Society (ACS)
SP - 8089-8100
IS - 12
VL - 86
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2021_Belaya,
author = {Maria A Belaya and Daniil A Knyazev and Denis D Borisov and Roman G. Novikov and Yury V. Tomilov},
title = {GaCl3-Mediated Cascade [2 + 4]-Cycloaddition/[4 + 2]-Annulation of Donor–Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.joc.1c00564},
number = {12},
pages = {8089--8100},
doi = {10.1021/acs.joc.1c00564}
}
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Belaya, Maria A., et al. “GaCl3-Mediated Cascade [2 + 4]-Cycloaddition/[4 + 2]-Annulation of Donor–Acceptor Cyclopropanes with Conjugated Dienes: Strategy for the Construction of Benzobicyclo[3.3.1]nonane Skeleton.” Journal of Organic Chemistry, vol. 86, no. 12, May. 2021, pp. 8089-8100. https://doi.org/10.1021/acs.joc.1c00564.
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