Journal of Organic Chemistry, volume 80, issue 16, pages 8225-8235
Donor–Acceptor Cyclopropanes as 1,2-Dipoles in GaCl3-Mediated [4 + 2]-Annulation with Alkenes: Easy Access to the Tetralin Skeleton
Roman G. Novikov
1, 2
,
Anna V Tarasova
1
,
Victor A Korolev
1
,
Evgeny V. Shulishov
1
,
Vladimir P Timofeev
2
,
Publication type: Journal Article
Publication date: 2015-07-31
Journal:
Journal of Organic Chemistry
Q2
Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
A new process for (4 + 2)-annulation of donor-acceptor cyclopropanes (DACs) with unsaturated compounds in the presence of anhydrous GaCl3 has been developed. In this process, DACs act as sources of formal 1,2- and 1,4-dipoles to give polysubstituted tetralins in high yields and with high regio- and diastereoselectivity. Alkenes with both aryl and alkyl substituents at the double bond undergo this reaction equally readily. A most likely mechanism of the reaction has been proposed. It involves preliminary generation of a key 1,2-dipolar gallium complex and its subsequent participation in annulation with an alkene.
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Novikov R. G. et al. Donor–Acceptor Cyclopropanes as 1,2-Dipoles in GaCl3-Mediated [4 + 2]-Annulation with Alkenes: Easy Access to the Tetralin Skeleton // Journal of Organic Chemistry. 2015. Vol. 80. No. 16. pp. 8225-8235.
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Novikov R. G., Tarasova A. V., Korolev V. A., Shulishov E. V., Timofeev V. P., Tomilov Y. V. Donor–Acceptor Cyclopropanes as 1,2-Dipoles in GaCl3-Mediated [4 + 2]-Annulation with Alkenes: Easy Access to the Tetralin Skeleton // Journal of Organic Chemistry. 2015. Vol. 80. No. 16. pp. 8225-8235.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.5b01179
UR - https://doi.org/10.1021/acs.joc.5b01179
TI - Donor–Acceptor Cyclopropanes as 1,2-Dipoles in GaCl3-Mediated [4 + 2]-Annulation with Alkenes: Easy Access to the Tetralin Skeleton
T2 - Journal of Organic Chemistry
AU - Novikov, Roman G.
AU - Tarasova, Anna V
AU - Korolev, Victor A
AU - Shulishov, Evgeny V.
AU - Timofeev, Vladimir P
AU - Tomilov, Yury V.
PY - 2015
DA - 2015/07/31
PB - American Chemical Society (ACS)
SP - 8225-8235
IS - 16
VL - 80
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2015_Novikov,
author = {Roman G. Novikov and Anna V Tarasova and Victor A Korolev and Evgeny V. Shulishov and Vladimir P Timofeev and Yury V. Tomilov},
title = {Donor–Acceptor Cyclopropanes as 1,2-Dipoles in GaCl3-Mediated [4 + 2]-Annulation with Alkenes: Easy Access to the Tetralin Skeleton},
journal = {Journal of Organic Chemistry},
year = {2015},
volume = {80},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.joc.5b01179},
number = {16},
pages = {8225--8235},
doi = {10.1021/acs.joc.5b01179}
}
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MLA
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Novikov, Roman G., et al. “Donor–Acceptor Cyclopropanes as 1,2-Dipoles in GaCl3-Mediated [4 + 2]-Annulation with Alkenes: Easy Access to the Tetralin Skeleton.” Journal of Organic Chemistry, vol. 80, no. 16, Jul. 2015, pp. 8225-8235. https://doi.org/10.1021/acs.joc.5b01179.