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
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
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.
Top-30
Citations by journals
1
2
3
4
5
|
|
Journal of Organic Chemistry
5 publications, 27.78%
|
|
Russian Chemical Bulletin
3 publications, 16.67%
|
|
Advanced Synthesis and Catalysis
3 publications, 16.67%
|
|
Tetrahedron Letters
2 publications, 11.11%
|
|
Organometallics
1 publication, 5.56%
|
|
Inorganic Chemistry
1 publication, 5.56%
|
|
Synthesis
1 publication, 5.56%
|
|
Molecular Catalysis
1 publication, 5.56%
|
|
Russian Chemical Reviews
1 publication, 5.56%
|
|
1
2
3
4
5
|
Citations by publishers
1
2
3
4
5
6
7
|
|
American Chemical Society (ACS)
7 publications, 38.89%
|
|
Springer Nature
3 publications, 16.67%
|
|
Elsevier
3 publications, 16.67%
|
|
Wiley
3 publications, 16.67%
|
|
Thieme
1 publication, 5.56%
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 5.56%
|
|
1
2
3
4
5
6
7
|
- 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.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2020,2021,2022,2023,2024],"ids":[0,0,0,0,0],"codes":[0,0,0,0,0],"imageUrls":["","","","",""],"datasets":[{"label":"Citations number","data":[3,8,1,4,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["16.67","44.44","5.56","22.22","11.11"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Journal of Organic Chemistry","Russian Chemical Bulletin","Advanced Synthesis and Catalysis","Tetrahedron Letters","Organometallics","Inorganic Chemistry","Synthesis","Molecular Catalysis","Russian Chemical Reviews"],"ids":[8697,10918,3906,6133,1409,24714,10934,4906,23802],"codes":[0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[5,3,3,2,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[27.78,16.67,16.67,11.11,5.56,5.56,5.56,5.56,5.56],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["American Chemical Society (ACS)","Springer Nature","Elsevier","Wiley","Thieme","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[40,8,17,11,135,9422],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[7,3,3,3,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[38.89,16.67,16.67,16.67,5.56,5.56],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0],"percentage":["0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[1,3,0,0,1],"percentage":["5.56","16.67","0","0","5.56"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,0,0,1,0],"percentage":["0","0","0","5.56","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[2,5,1,3,1],"percentage":["11.11","27.78","5.56","16.67","5.56"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0,0],"percentage":["0","0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0,0],"percentage":["0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[1,3,0,0,1],"percentage":["5.56","16.67","0","0","5.56"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,0,0,2,0],"percentage":["5.56","0","0","11.11","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,5,1,2,1],"percentage":["5.56","27.78","5.56","11.11","5.56"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0,0],"percentage":["0","0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
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.
GOST all authors (up to 50)
Copy
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.
Cite this
RIS
Copy
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 00:00:00
PB - American Chemical Society (ACS)
SP - 6174-6182
IS - 10
VL - 84
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex
Copy
@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}
}
Cite this
MLA
Copy
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.
Profiles