Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines.
Publication type: Journal Article
Publication date: 2021-09-14
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
34517699
Organic Chemistry
Abstract
We report on a facile method for the preparation of 2-benzoxepine derivatives as a result of Rh(II)-catalyzed decomposition of diazo arylidene succinimides in the presence of aldehydes. The process is thought to involve the formation of styryl carbonyl ylide which undergoes 1,7-electrocyclization and subsequent 1,5-hydrogen shift. In some cases, the competition of the target reaction and [3+2] dipolar cycloaddition of the intermediate carbonyl ylide to another molecule of diazo substrate was observed. Generally, the desired 2-benzoxepines were isolated in good to high yields and high diastereoselectivity. The developed original approach toward a 2-benzoxepine core via formal [5+2] cycloaddition of styryl carbenoids and aldehydes significantly expands the arsenal of synthetic methods for producing this scaffold.
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Total citations:
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Citations from 2024:
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(40%)
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GOST
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Inyutina A. et al. Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines. // Journal of Organic Chemistry. 2021. Vol. 86. No. 19. pp. 13673-13683.
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Inyutina A., Kantin G., Dar’in D., Krasavin M. Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines. // Journal of Organic Chemistry. 2021. Vol. 86. No. 19. pp. 13673-13683.
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TY - JOUR
DO - 10.1021/acs.joc.1c01710
UR - https://doi.org/10.1021/acs.joc.1c01710
TI - Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines.
T2 - Journal of Organic Chemistry
AU - Inyutina, Anna
AU - Kantin, Grigory
AU - Dar’in, Dmitry
AU - Krasavin, Mikhail
PY - 2021
DA - 2021/09/14
PB - American Chemical Society (ACS)
SP - 13673-13683
IS - 19
VL - 86
PMID - 34517699
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2021_Inyutina,
author = {Anna Inyutina and Grigory Kantin and Dmitry Dar’in and Mikhail Krasavin},
title = {Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines.},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.joc.1c01710},
number = {19},
pages = {13673--13683},
doi = {10.1021/acs.joc.1c01710}
}
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MLA
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Inyutina, Anna, et al. “Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines..” Journal of Organic Chemistry, vol. 86, no. 19, Sep. 2021, pp. 13673-13683. https://doi.org/10.1021/acs.joc.1c01710.
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