Angewandte Chemie - International Edition, volume 55, issue 40, pages 12233-12237
GaCl3 -Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes
Publication type: Journal Article
Publication date: 2016-08-30
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
A new strategy for cascade assembly of substituted indenes and polycyclic lactones based on reactions of donor-acceptor cyclopropanes and styrylmalonates with aromatic aldehydes in the presence of GaCl3 has been developed. The use of GaCl3 makes it possible to principally change the direction of the reaction known in this series of substrates and to perform the process in a multicomponent version. Generation of formal 1,2-zwitterionic intermediates owing to complexation of dicarboxylate groups with GaCl3 is the driving force of the reactions discovered. This method makes it possible to assemble indenylmalonates or indano[1',2':2,3]indano[2,1-b]furan-2-ones in one synthetic stage from readily available starting compounds with high regio- and diastereoselectivity. A mechanism of the reactions has been suggested using the (18) O label in benzaldehyde.
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5
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15
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25
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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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Borisov D. D. et al. GaCl3 -Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes // Angewandte Chemie - International Edition. 2016. Vol. 55. No. 40. pp. 12233-12237.
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Borisov D. D., Novikov R. G., Tomilov Y. V. GaCl3 -Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes // Angewandte Chemie - International Edition. 2016. Vol. 55. No. 40. pp. 12233-12237.
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TY - JOUR
DO - 10.1002/anie.201603927
UR - https://doi.org/10.1002/anie.201603927
TI - GaCl3 -Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes
T2 - Angewandte Chemie - International Edition
AU - Borisov, Denis D
AU - Tomilov, Yury V.
AU - Novikov, Roman G.
PY - 2016
DA - 2016/08/30 00:00:00
PB - Wiley
SP - 12233-12237
IS - 40
VL - 55
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2016_Borisov,
author = {Denis D Borisov and Yury V. Tomilov and Roman G. Novikov},
title = {GaCl3 -Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes},
journal = {Angewandte Chemie - International Edition},
year = {2016},
volume = {55},
publisher = {Wiley},
month = {aug},
url = {https://doi.org/10.1002/anie.201603927},
number = {40},
pages = {12233--12237},
doi = {10.1002/anie.201603927}
}
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MLA
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Borisov, Denis D., et al. “GaCl3 -Mediated Reactions of Donor-Acceptor Cyclopropanes with Aromatic Aldehydes.” Angewandte Chemie - International Edition, vol. 55, no. 40, Aug. 2016, pp. 12233-12237. https://doi.org/10.1002/anie.201603927.
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