Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids
Publication type: Journal Article
Publication date: 2019-08-06
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A unique example of the one‐pot trans‐diastereoselective reaction of meso‐tricyclic anhydrides is reported. The process involves anhydride ring opening by an amidoxime and the sequential cis‐ to trans‐ epimerization/cyclodehydration of the O‐acylamidoxime intermediate. The resulted 1,2,4‐oxadiazole/norborna(e)ne hybrids are obtained in moderate to good yields and > 95 % diastereomeric excess without any additional purifications. These compounds are interesting not only for drug discovery but for other chemistry‐related fields due to the presence of two easily modifiable moieties.
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Baykov S. V. et al. Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 33. pp. 5685-5693.
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Baykov S. V., Tarasenko M., Zelenkov L. E., Kasatkina S. O., Savko P., Shetnev A. A. Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 33. pp. 5685-5693.
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TY - JOUR
DO - 10.1002/EJOC.201900843
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900843
TI - Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids
T2 - European Journal of Organic Chemistry
AU - Baykov, Sergey V
AU - Tarasenko, Marina
AU - Zelenkov, Lev E
AU - Kasatkina, Svetlana O.
AU - Savko, Polina
AU - Shetnev, Anton A
PY - 2019
DA - 2019/08/06
PB - Wiley
SP - 5685-5693
IS - 33
VL - 2019
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2019_Baykov,
author = {Sergey V Baykov and Marina Tarasenko and Lev E Zelenkov and Svetlana O. Kasatkina and Polina Savko and Anton A Shetnev},
title = {Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids},
journal = {European Journal of Organic Chemistry},
year = {2019},
volume = {2019},
publisher = {Wiley},
month = {aug},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900843},
number = {33},
pages = {5685--5693},
doi = {10.1002/EJOC.201900843}
}
Cite this
MLA
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Baykov, Sergey V., et al. “Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids.” European Journal of Organic Chemistry, vol. 2019, no. 33, Aug. 2019, pp. 5685-5693. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900843.