Organic and Biomolecular Chemistry, volume 19, issue 26, pages 5702-5724

Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles

Julien Caille ^{1, 2}

Julien Caillé ^{1, 2}

Raphaël Robiette ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Institute of Condensed Matter and Nanosciences, Université Catholique de Louvain, Place Louis Pasteur 1 Box L4.01.02, 1348 Louvain-la-Neuve, Belgium |

Institut de Chimie et des Matériaux Paris Est (ICMPE), UMR-CNRS 7182, Université Paris Est Créteil (UPEC), 2 Rue Henri Dunant, 94320 Thiais, France |

Publication type: Journal Article

Publication date: 2021-06-07

Royal Society of Chemistry (RSC)

Journal: Organic and Biomolecular Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 3.2

ISSN: 14770520, 14770539

DOI: 10.1039/d1ob00838b

Copy DOI

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

The stereocontrolled formation of medium-sized carbocycles is a major goal in modern organic chemistry due to their widespread occurrence in natural products and pharmaceutically active ingredients. One approach consists in the use of cycloaddition reactions which notably results in high selectivities and atom-economy. To this end, cyclopropanes are ideal substrates since they can provide readily functionalized three- or five-carbon synthons. Herein we report advances made in cycloaddition reactions of cyclopropanes towards the synthesis of medium-sized carbocycles via transition metal catalysis or Lewis acid catalysis.

By date By citations

Top-30

Citations by journals

	1 2 3 4 5
Organic Letters	Organic Letters, 5, 13.89% Organic Letters 5 publications, 13.89%
Journal of Organic Chemistry	Journal of Organic Chemistry, 5, 13.89% Journal of Organic Chemistry 5 publications, 13.89%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 3, 8.33% Organic and Biomolecular Chemistry 3 publications, 8.33%
Journal of the American Chemical Society	Journal of the American Chemical Society, 2, 5.56% Journal of the American Chemical Society 2 publications, 5.56%
ACS Catalysis	ACS Catalysis, 2, 5.56% ACS Catalysis 2 publications, 5.56%
Chemical Communications	Chemical Communications, 2, 5.56% Chemical Communications 2 publications, 5.56%
New Journal of Chemistry	New Journal of Chemistry, 2, 5.56% New Journal of Chemistry 2 publications, 5.56%
Synthesis	Synthesis, 2, 5.56% Synthesis 2 publications, 5.56%
Synlett	Synlett, 2, 5.56% Synlett 2 publications, 5.56%
Bulletin of the Chemical Society of Japan	Bulletin of the Chemical Society of Japan, 1, 2.78% Bulletin of the Chemical Society of Japan 1 publication, 2.78%
Molecules	Molecules, 1, 2.78% Molecules 1 publication, 2.78%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 2.78% European Journal of Organic Chemistry 1 publication, 2.78%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 1, 2.78% Asian Journal of Organic Chemistry 1 publication, 2.78%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 1, 2.78% Angewandte Chemie - International Edition 1 publication, 2.78%
Angewandte Chemie	Angewandte Chemie, 1, 2.78% Angewandte Chemie 1 publication, 2.78%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 1, 2.78% Organic Chemistry Frontiers 1 publication, 2.78%
Chemical Society Reviews	Chemical Society Reviews, 1, 2.78% Chemical Society Reviews 1 publication, 2.78%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 2.78% Russian Chemical Reviews 1 publication, 2.78%
ACS Central Science	ACS Central Science, 1, 2.78% ACS Central Science 1 publication, 2.78%
Science China Chemistry	Science China Chemistry, 1, 2.78% Science China Chemistry 1 publication, 2.78%
	1 2 3 4 5

Citations by publishers

	2 4 6 8 10 12 14 16
American Chemical Society (ACS)	American Chemical Society (ACS), 15, 41.67% American Chemical Society (ACS) 15 publications, 41.67%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 9, 25% Royal Society of Chemistry (RSC) 9 publications, 25%
Wiley	Wiley, 4, 11.11% Wiley 4 publications, 11.11%
Thieme	Thieme, 4, 11.11% Thieme 4 publications, 11.11%
The Chemical Society of Japan	The Chemical Society of Japan, 1, 2.78% The Chemical Society of Japan 1 publication, 2.78%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 2.78% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 2.78%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 2.78% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 2.78%
Springer Nature	Springer Nature, 1, 2.78% Springer Nature 1 publication, 2.78%
	2 4 6 8 10 12 14 16

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":[2021,2022,2023,2024],"ids":[0,0,0,0],"codes":[0,0,0,0],"imageUrls":["","","",""],"datasets":[{"label":"Citations number","data":[7,11,10,8],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["19.44","30.56","27.78","22.22"],"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 Letters","Journal of Organic Chemistry","Organic and Biomolecular Chemistry","Journal of the American Chemical Society","ACS Catalysis","Chemical Communications","New Journal of Chemistry","Synthesis","Synlett","Bulletin of the Chemical Society of Japan","Molecules","European Journal of Organic Chemistry","Asian Journal of Organic Chemistry","Angewandte Chemie - International Edition","Angewandte Chemie","Organic Chemistry Frontiers","Chemical Society Reviews","Russian Chemical Reviews","ACS Central Science","Science China Chemistry"],"ids":[3315,8697,541,4813,4873,9073,1404,10934,10217,20870,1770,19472,9409,19215,25450,3991,20586,23802,4900,14409],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/ktSZPrGjOMvauY6mn7jk8bqo3Af0S6abv653w90B_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp"],"datasets":[{"label":"","data":[5,5,3,2,2,2,2,2,2,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[13.89,13.89,8.33,5.56,5.56,5.56,5.56,5.56,5.56,2.78,2.78,2.78,2.78,2.78,2.78,2.78,2.78,2.78,2.78,2.78],"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)","Royal Society of Chemistry (RSC)","Wiley","Thieme","The Chemical Society of Japan","Multidisciplinary Digital Publishing Institute (MDPI)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii","Springer Nature"],"ids":[40,123,11,135,6950,202,9422,8],"codes":[0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/ktSZPrGjOMvauY6mn7jk8bqo3Af0S6abv653w90B_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp"],"datasets":[{"label":"","data":[15,9,4,4,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[41.67,25,11.11,11.11,2.78,2.78,2.78,2.78],"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":[2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0],"percentage":["0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,0],"percentage":["0","0","0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[2,1,1,2],"percentage":["5.56","2.78","2.78","5.56"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[5,10,9,6],"percentage":["13.89","27.78","25","16.67"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0,0,0],"percentage":["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":[2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,0,0],"percentage":["0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0,0,2],"percentage":["0","0","0","5.56"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[4,3,6,0],"percentage":["11.11","8.33","16.67","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[3,7,4,6],"percentage":["8.33","19.44","11.11","16.67"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,1,0,0],"percentage":["0","2.78","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 |

Cite this

GOST Copy

Caille J. et al. Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 26. pp. 5702-5724.

GOST all authors (up to 50) Copy

Caille J., Caillé J., Robiette R. Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 26. pp. 5702-5724.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/d1ob00838b

UR - https://doi.org/10.1039/d1ob00838b

TI - Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles

T2 - Organic and Biomolecular Chemistry

AU - Caille, Julien

AU - Robiette, Raphaël

AU - Caillé, Julien

PY - 2021

DA - 2021/06/07 00:00:00

PB - Royal Society of Chemistry (RSC)

SP - 5702-5724

IS - 26

VL - 19

SN - 1477-0520

SN - 1477-0539

ER -

BibTex |

Cite this

BibTex Copy

@article{2021_Caille,

author = {Julien Caille and Raphaël Robiette and Julien Caillé},

title = {Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles},

journal = {Organic and Biomolecular Chemistry},

year = {2021},

volume = {19},

publisher = {Royal Society of Chemistry (RSC)},

month = {jun},

url = {https://doi.org/10.1039/d1ob00838b},

number = {26},

pages = {5702--5724},

doi = {10.1039/d1ob00838b}

}

MLA

Cite this

MLA Copy

Caille, Julien, et al. “Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles.” Organic and Biomolecular Chemistry, vol. 19, no. 26, Jun. 2021, pp. 5702-5724. https://doi.org/10.1039/d1ob00838b.

Found error?

Publisher

Royal Society of Chemistry (RSC)

Journal

Organic and Biomolecular Chemistry

Quartile SCImago

Quartile WOS

Impact factor

3.2

ISSN

14770520 (Print)
14770539 (Electronic)