Journal of Organic Chemistry, volume 87, issue 12, pages 7905-7918
Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters
Publication type: Journal Article
Publication date: 2022-06-03
Journal:
Journal of Organic Chemistry
Q2
Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Herein, we report a straightforward one-pot synthesis of tetrahydrofurobenzopyran and tetrahydrofurobenzofuran systems via an in situ ring-expansion of the cyclopropane carbaldehydes followed by a [2 + n] cycloaddition with the quinone derivatives. The transformation not only unveils a new reaction mode of cyclopropane carbaldehydes with quinone methides/esters, but also promotes a step-efficient diastereoselective route to the sophisticatedly fused oxygen tricycles that can be further dehydrogenated to access the valued dihydro-2H-furo[2,3-b]chromene frameworks.
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Kaur N. et al. Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters // Journal of Organic Chemistry. 2022. Vol. 87. No. 12. pp. 7905-7918.
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Kaur N., Kumar P., Dutt S., Banerjee P. Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters // Journal of Organic Chemistry. 2022. Vol. 87. No. 12. pp. 7905-7918.
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TY - JOUR
DO - 10.1021/acs.joc.2c00566
UR - https://doi.org/10.1021/acs.joc.2c00566
TI - Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters
T2 - Journal of Organic Chemistry
AU - Kaur, Navpreet
AU - Kumar, Pankaj
AU - Dutt, Shiv
AU - Banerjee, Prabal
PY - 2022
DA - 2022/06/03
PB - American Chemical Society (ACS)
SP - 7905-7918
IS - 12
VL - 87
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2022_Kaur,
author = {Navpreet Kaur and Pankaj Kumar and Shiv Dutt and Prabal Banerjee},
title = {Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.joc.2c00566},
number = {12},
pages = {7905--7918},
doi = {10.1021/acs.joc.2c00566}
}
Cite this
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Kaur, Navpreet, et al. “Accessing Complex Tetrahydrofurobenzo-Pyran/Furan Scaffolds via Lewis-Acid Catalyzed Bicyclization of Cyclopropane Carbaldehydes with Quinone Methides/Esters.” Journal of Organic Chemistry, vol. 87, no. 12, Jun. 2022, pp. 7905-7918. https://doi.org/10.1021/acs.joc.2c00566.