Advanced Synthesis and Catalysis, volume 364, issue 2, pages 426-439
Asymmetric Conjugate Addition of 3‐Hydroxychromen‐4‐Ones to Electron‐Deficient Olefins Catalyzed by Recyclable C 2 ‐Symmetric Squaramide
Publication type: Journal Article
Publication date: 2021-10-28
Journal:
Advanced Synthesis and Catalysis
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.4
ISSN: 16154150, 16154169
General Chemistry
Abstract
The readily scalable asymmetric synthesis of the chiral chromone derivatives functionalized at position 2 via electrophilic enantioselective olefination of the chromone core with nitroolefins and ß,γ-unsaturated α-ketoesters in the presence of simple C2-symmetric tertiary amine-squaramide catalyst was developed. The reaction products were obtained in 80–99% yield with 89–99% ee in 95% EtOH. The absolute configurations of the synthesized chromone derivatives were unambiguously established by transformation of compound (R)-3 aa to known methyl (R)-β-nitro-α-phenylpropionate and by the single crystal XRD analysis of compounds (R,S)-5 aa and (R,S)-5 ab. Catalyst V poorly soluble in common organic solvents could be easily separated from the reaction mixture and reused up to 10 catalytic cycles. Catalytic hydrogenation and esterification reactions of the synthesized compounds were carried out to demonstrate synthetic potential of the developed procedure.
Citations by journals
|
1
2
|
|
|
Advanced Synthesis and Catalysis
|
Advanced Synthesis and Catalysis
2 publications, 33.33%
|
|
Russian Chemical Bulletin
|
Russian Chemical Bulletin
1 publication, 16.67%
|
|
Catalysts
|
Catalysts
1 publication, 16.67%
|
|
Electrophoresis
|
Electrophoresis
1 publication, 16.67%
|
|
Organic and Biomolecular Chemistry
|
Organic and Biomolecular Chemistry
1 publication, 16.67%
|
|
1
2
|
Citations by publishers
|
1
2
3
|
|
|
Wiley
|
Wiley
3 publications, 50%
|
|
Springer Nature
|
Springer Nature
1 publication, 16.67%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 16.67%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
1 publication, 16.67%
|
|
1
2
3
|
- We do not take into account publications that 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":[2022,2023],"ids":[0,0],"codes":[0,0],"imageUrls":["",""],"datasets":[{"label":"Citations number","data":[2,4],"backgroundColor":["#3B82F6","#3B82F6"],"percentage":["33.33","66.67"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"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":["Advanced Synthesis and Catalysis","Russian Chemical Bulletin","Catalysts","Electrophoresis","Organic and Biomolecular Chemistry"],"ids":[3906,10918,3739,23809,541],"codes":[0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.33,16.67,16.67,16.67,16.67],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"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":["Wiley","Springer Nature","Multidisciplinary Digital Publishing Institute (MDPI)","Royal Society of Chemistry (RSC)"],"ids":[11,8,202,123],"codes":[0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[3,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[50,16.67,16.67,16.67],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Kovalevsky R. A. et al. Asymmetric Conjugate Addition of 3‐Hydroxychromen‐4‐Ones to Electron‐Deficient Olefins Catalyzed by Recyclable C 2 ‐Symmetric Squaramide // Advanced Synthesis and Catalysis. 2021. Vol. 364. No. 2. pp. 426-439.
GOST all authors (up to 50)
Copy
Kovalevsky R. A., Kucherenko A., Korlyukov A., Zlotin S. G. Asymmetric Conjugate Addition of 3‐Hydroxychromen‐4‐Ones to Electron‐Deficient Olefins Catalyzed by Recyclable C 2 ‐Symmetric Squaramide // Advanced Synthesis and Catalysis. 2021. Vol. 364. No. 2. pp. 426-439.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/adsc.202101019
UR - https://doi.org/10.1002%2Fadsc.202101019
TI - Asymmetric Conjugate Addition of 3‐Hydroxychromen‐4‐Ones to Electron‐Deficient Olefins Catalyzed by Recyclable C 2 ‐Symmetric Squaramide
T2 - Advanced Synthesis and Catalysis
AU - Kovalevsky, Ruslan A
AU - Zlotin, Sergei G
AU - Kucherenko, Alexander
AU - Korlyukov, Alexander
PY - 2021
DA - 2021/10/28 00:00:00
PB - Wiley
SP - 426-439
IS - 2
VL - 364
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex
Copy
@article{2021_Kovalevsky,
author = {Ruslan A Kovalevsky and Sergei G Zlotin and Alexander Kucherenko and Alexander Korlyukov},
title = {Asymmetric Conjugate Addition of 3‐Hydroxychromen‐4‐Ones to Electron‐Deficient Olefins Catalyzed by Recyclable C 2 ‐Symmetric Squaramide},
journal = {Advanced Synthesis and Catalysis},
year = {2021},
volume = {364},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002%2Fadsc.202101019},
number = {2},
pages = {426--439},
doi = {10.1002/adsc.202101019}
}
Cite this
MLA
Copy
Kovalevsky, Ruslan A., et al. “Asymmetric Conjugate Addition of 3‐Hydroxychromen‐4‐Ones to Electron‐Deficient Olefins Catalyzed by Recyclable C 2 ‐Symmetric Squaramide.” Advanced Synthesis and Catalysis, vol. 364, no. 2, Oct. 2021, pp. 426-439. https://doi.org/10.1002%2Fadsc.202101019.
Profiles