Journal of Organic Chemistry, volume 87, issue 5, pages 3079-3088
Methylene Capping Facilitates Cross-Metathesis Reactions of Enals: A Short Synthesis of 7-Methoxywutaifuranal from the Xylochemical Isoeugenol
1
Institut fuer Chemie, Universitaet Potsdam, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany
|
Publication type: Journal Article
Publication date: 2022-01-17
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Four combinations of type-I olefins isoeugenol and 4-hydroxy-3-methoxystyrene with type-II olefins acrolein and crotonaldehyde were investigated in cross-metathesis (CM) reactions. While both type-I olefins are suitable CM partners for this transformation, we observed synthetically useful conversions only with type-II olefin crotonaldehyde. For economic reasons, isoeugenol, a cheap xylochemical available from renewable lignocellulose or from clove oil, is the preferred type-I CM partner. Nearly quantitative conversions to coniferyl aldehyde by the CM reaction of isoeugenol and crotonaldehyde can be obtained at ambient temperature without a solvent or at high substrate concentrations of 2 mol·L-1 with the second-generation Hoveyda-Grubbs catalyst. Under these conditions, the ratio of reactants can be reduced to 1:1.5 and catalyst loadings as low as 0.25 mol % are possible. The high reactivity of the isoeugenol/crotonaldehyde combination in olefin metathesis reactions was demonstrated by a short synthesis of the natural product 7-methoxywutaifuranal, which was obtained from isoeugenol in a 44% yield over five steps. We suggest that the superior performance of crotonaldehyde in the CM reactions investigated can be rationalized by "methylene capping", i.e., the steric stabilization of the propagating Ru-alkylidene species.
Top-30
Citations by journals
|
1
|
|
|
Molecules
1 publication, 33.33%
|
|
|
Journal of Organic Chemistry
1 publication, 33.33%
|
|
|
Russian Chemical Reviews
1 publication, 33.33%
|
|
|
1
|
Citations by publishers
|
1
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 33.33%
|
|
|
American Chemical Society (ACS)
1 publication, 33.33%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 33.33%
|
|
|
1
|
- 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":[2023,2024],"ids":[0,0],"codes":[0,0],"imageUrls":["",""],"datasets":[{"label":"Citations number","data":[2,1],"backgroundColor":["#3B82F6","#3B82F6"],"percentage":["66.67","33.33"],"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":["Molecules","Journal of Organic Chemistry","Russian Chemical Reviews"],"ids":[1770,8697,23802],"codes":[0,0,0],"imageUrls":["\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.33,33.33,33.33],"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":["Multidisciplinary Digital Publishing Institute (MDPI)","American Chemical Society (ACS)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii"],"ids":[202,40,9422],"codes":[0,0,0],"imageUrls":["\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp"],"datasets":[{"label":"","data":[1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.33,33.33,33.33],"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":[2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0],"percentage":["0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0],"percentage":["0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,0],"percentage":["0","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[2,1],"percentage":["66.67","33.33"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0],"percentage":["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":[2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0],"percentage":["0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[0,0],"percentage":["0","0"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,0],"percentage":["33.33","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,1],"percentage":["33.33","33.33"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[0,0],"percentage":["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
Lood K. et al. Methylene Capping Facilitates Cross-Metathesis Reactions of Enals: A Short Synthesis of 7-Methoxywutaifuranal from the Xylochemical Isoeugenol // Journal of Organic Chemistry. 2022. Vol. 87. No. 5. pp. 3079-3088.
GOST all authors (up to 50)
Copy
Lood K., Tikk T., Krüger M., Schmidt B. Methylene Capping Facilitates Cross-Metathesis Reactions of Enals: A Short Synthesis of 7-Methoxywutaifuranal from the Xylochemical Isoeugenol // Journal of Organic Chemistry. 2022. Vol. 87. No. 5. pp. 3079-3088.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.1c02851
UR - https://doi.org/10.1021/acs.joc.1c02851
TI - Methylene Capping Facilitates Cross-Metathesis Reactions of Enals: A Short Synthesis of 7-Methoxywutaifuranal from the Xylochemical Isoeugenol
T2 - Journal of Organic Chemistry
AU - Lood, Kajsa
AU - Tikk, Triin
AU - Krüger, Mandy
AU - Schmidt, Bernd
PY - 2022
DA - 2022/01/17 00:00:00
PB - American Chemical Society (ACS)
SP - 3079-3088
IS - 5
VL - 87
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex
Copy
@article{2022_Lood,
author = {Kajsa Lood and Triin Tikk and Mandy Krüger and Bernd Schmidt},
title = {Methylene Capping Facilitates Cross-Metathesis Reactions of Enals: A Short Synthesis of 7-Methoxywutaifuranal from the Xylochemical Isoeugenol},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.joc.1c02851},
number = {5},
pages = {3079--3088},
doi = {10.1021/acs.joc.1c02851}
}
Cite this
MLA
Copy
Lood, Kajsa, et al. “Methylene Capping Facilitates Cross-Metathesis Reactions of Enals: A Short Synthesis of 7-Methoxywutaifuranal from the Xylochemical Isoeugenol.” Journal of Organic Chemistry, vol. 87, no. 5, Jan. 2022, pp. 3079-3088. https://doi.org/10.1021/acs.joc.1c02851.