Angewandte Chemie - International Edition, volume 61, issue 29
Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis
Publication type: Journal Article
Publication date: 2022-05-31
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
A novel enantioselective (8+3) cycloaddition between donor-acceptor cyclopropanes and heptafulvenoids catalysed by a chiral bifunctional Brønsted base is described. Importantly, the reaction, which leverages an anionic activation strategy, is divergent from prototypical Lewis-acid activation protocols. A series of cyclopropylketones react with tropones affording the desired (8+3) cycloadducts in high yield and enantiomeric excess. For barbiturate substituted heptafulvenes, the (8+3) cycloaddition with cyclopropylketones proceeds in good yield, excellent diastereoselectivity and high enantiomeric excess. The experimental work is supported by DFT calculations, which indicate that the bifunctional organocatalyst activates both the donor-acceptor cyclopropane and tropone; the reaction proceeds in a step-wise manner with the ring-closure being the stereodetermining step
Top-30
Citations by journals
|
1
2
|
|
|
Organic Chemistry Frontiers
2 publications, 10.53%
|
|
|
Journal of Organic Chemistry
2 publications, 10.53%
|
|
|
Organic Letters
2 publications, 10.53%
|
|
|
Synfacts
1 publication, 5.26%
|
|
|
Catalysts
1 publication, 5.26%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 5.26%
|
|
|
Tetrahedron Chem
1 publication, 5.26%
|
|
|
ACS Omega
1 publication, 5.26%
|
|
|
Molecular Catalysis
1 publication, 5.26%
|
|
|
Progress in Heterocyclic Chemistry
1 publication, 5.26%
|
|
|
Synlett
1 publication, 5.26%
|
|
|
European Journal of Organic Chemistry
1 publication, 5.26%
|
|
|
Russian Chemical Reviews
1 publication, 5.26%
|
|
|
Industrial & Engineering Chemistry Research
1 publication, 5.26%
|
|
|
Angewandte Chemie
1 publication, 5.26%
|
|
|
Angewandte Chemie - International Edition
1 publication, 5.26%
|
|
|
1
2
|
Citations by publishers
|
1
2
3
4
5
6
|
|
|
American Chemical Society (ACS)
6 publications, 31.58%
|
|
|
Wiley
4 publications, 21.05%
|
|
|
Elsevier
3 publications, 15.79%
|
|
|
Thieme
2 publications, 10.53%
|
|
|
Royal Society of Chemistry (RSC)
2 publications, 10.53%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 5.26%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 5.26%
|
|
|
1
2
3
4
5
6
|
- 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":[2022,2023,2024],"ids":[0,0,0],"codes":[0,0,0],"imageUrls":["","",""],"datasets":[{"label":"Citations number","data":[2,9,8],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6"],"percentage":["10.53","47.37","42.11"],"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":["Organic Chemistry Frontiers","Journal of Organic Chemistry","Organic Letters","Synfacts","Catalysts","Advanced Synthesis and Catalysis","Tetrahedron Chem","ACS Omega","Molecular Catalysis","Progress in Heterocyclic Chemistry","Synlett","European Journal of Organic Chemistry","Russian Chemical Reviews","Industrial & Engineering Chemistry Research","Angewandte Chemie","Angewandte Chemie - International Edition"],"ids":[3991,8697,3315,25513,3739,3906,36165,18901,4906,17224,10217,19472,23802,12141,25450,19215],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp"],"datasets":[{"label":"","data":[2,2,2,1,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[10.53,10.53,10.53,5.26,5.26,5.26,5.26,5.26,5.26,5.26,5.26,5.26,5.26,5.26,5.26,5.26],"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)","Wiley","Elsevier","Thieme","Royal Society of Chemistry (RSC)","Multidisciplinary Digital Publishing Institute (MDPI)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[40,11,17,135,123,202,9422],"codes":[0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[6,4,3,2,2,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[31.58,21.05,15.79,10.53,10.53,5.26,5.26],"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":[2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0],"percentage":["0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0],"percentage":["0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,3,1],"percentage":["0","15.79","5.26"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,4,7],"percentage":["5.26","21.05","36.84"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,2,0],"percentage":["5.26","10.53","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":[2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0],"percentage":["0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,1,0],"percentage":["0","5.26","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,3,2],"percentage":["0","15.79","10.53"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,3,5],"percentage":["5.26","15.79","26.32"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,2,1],"percentage":["5.26","10.53","5.26"]}]},"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
Cite this
GOST
Copy
Mcleod D. et al. Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 29.
GOST all authors (up to 50)
Copy
Mcleod D., Thøgersen M. K., Barløse C. L., Skipper M. L., Obregón E. B., Kaasen Jørgensen K. Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 29.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.202206096
UR - https://doi.org/10.1002/anie.202206096
TI - Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis
T2 - Angewandte Chemie - International Edition
AU - Skipper, Mette Louise
AU - Obregón, Erlaitz Basabe
AU - Mcleod, David
AU - Thøgersen, Mathias Kirk
AU - Barløse, Casper Larsen
AU - Kaasen Jørgensen, K.
PY - 2022
DA - 2022/05/31 00:00:00
PB - Wiley
IS - 29
VL - 61
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex
Copy
@article{2022_Mcleod,
author = {Mette Louise Skipper and Erlaitz Basabe Obregón and David Mcleod and Mathias Kirk Thøgersen and Casper Larsen Barløse and K. Kaasen Jørgensen},
title = {Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis},
journal = {Angewandte Chemie - International Edition},
year = {2022},
volume = {61},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/anie.202206096},
number = {29},
doi = {10.1002/anie.202206096}
}