Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines.
Aleksandr O Kokuev
1, 2
,
Yulia A Antonova
1, 3
,
Valentin S Dorokhov
1, 2
,
Ivan S Golovanov
1
,
Andrey A Tabolin
1
,
Publication type: Journal Article
Publication date: 2018-08-01
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30067029
Organic Chemistry
Abstract
Acylation of nitronates affords α-acyloxyoxime derivatives via an umpolung functionalization of the α-position. This transformation involves generation of hitherto unknown N-acyloxy, N-oxyenamines and their fast [3,3]-sigmatropic rearrangement driven by the cleavage of the weak N-O bond. The reaction has a broad scope, and it is regioselective in the case of nitronates possessing nonsymmetrically substituted α-positions. Application to the formal total synthesis of clausenamide and cis-clausenamide is presented.
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GOST
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Kokuev A. O. et al. Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines. // Journal of Organic Chemistry. 2018. Vol. 83. No. 18. pp. 11057-11066.
GOST all authors (up to 50)
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Kokuev A. O., Antonova Y. A., Dorokhov V. S., Golovanov I. S., Nelyubina Y. V., Tabolin A. A., Sukhorukov A. Yu., Ioffe S. L. Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines. // Journal of Organic Chemistry. 2018. Vol. 83. No. 18. pp. 11057-11066.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.8b01652
UR - https://doi.org/10.1021/acs.joc.8b01652
TI - Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines.
T2 - Journal of Organic Chemistry
AU - Kokuev, Aleksandr O
AU - Antonova, Yulia A
AU - Dorokhov, Valentin S
AU - Golovanov, Ivan S
AU - Nelyubina, Yulia V.
AU - Tabolin, Andrey A
AU - Sukhorukov, Alexey Yu
AU - Ioffe, Sema L.
PY - 2018
DA - 2018/08/01
PB - American Chemical Society (ACS)
SP - 11057-11066
IS - 18
VL - 83
PMID - 30067029
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Kokuev,
author = {Aleksandr O Kokuev and Yulia A Antonova and Valentin S Dorokhov and Ivan S Golovanov and Yulia V. Nelyubina and Andrey A Tabolin and Alexey Yu Sukhorukov and Sema L. Ioffe},
title = {Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines.},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.joc.8b01652},
number = {18},
pages = {11057--11066},
doi = {10.1021/acs.joc.8b01652}
}
Cite this
MLA
Copy
Kokuev, Aleksandr O., et al. “Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines..” Journal of Organic Chemistry, vol. 83, no. 18, Aug. 2018, pp. 11057-11066. https://doi.org/10.1021/acs.joc.8b01652.