Journal of Organic Chemistry, volume 84, issue 10, pages 6174-6182
Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones
Publication type: Journal Article
Publication date: 2019-04-17
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 cascade three-component process for high trans,trans-diastereoselective assembly of five-membered (1-halovinyl)lactones has been developed. The process is based on reactions of substituted methylidenemalonates and cyclopropanedicarboxylates with 3-haloprop-1-ynes in the presence of GaHal3 and involves the intermediate in situ generation of 1,2-zwitterionic gallium complexes with [Ga(L)3]3+[GaX4-]3 composition. Chloro, bromo, and iodo derivatives can be obtained successfully. Mechanistic and stereochemical aspects of the process we developed have been studied and considered in detail.
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Denisov D. A. et al. Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones // Journal of Organic Chemistry. 2019. Vol. 84. No. 10. pp. 6174-6182.
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Denisov D. A., Borisov D. D., Korolev V. A., Novikov R. G., Tomilov Y. V. Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones // Journal of Organic Chemistry. 2019. Vol. 84. No. 10. pp. 6174-6182.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.9b00354
UR - https://doi.org/10.1021/acs.joc.9b00354
TI - Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones
T2 - Journal of Organic Chemistry
AU - Denisov, Dmitry A
AU - Borisov, Denis D
AU - Korolev, Victor A
AU - Novikov, Roman G.
AU - Tomilov, Yury V.
PY - 2019
DA - 2019/04/17
PB - American Chemical Society (ACS)
SP - 6174-6182
IS - 10
VL - 84
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2019_Denisov,
author = {Dmitry A Denisov and Denis D Borisov and Victor A Korolev and Roman G. Novikov and Yury V. Tomilov},
title = {Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.joc.9b00354},
number = {10},
pages = {6174--6182},
doi = {10.1021/acs.joc.9b00354}
}
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MLA
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Denisov, Dmitry A., et al. “Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones.” Journal of Organic Chemistry, vol. 84, no. 10, Apr. 2019, pp. 6174-6182. https://doi.org/10.1021/acs.joc.9b00354.
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