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Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy,N-oxyenamines Full article

Journal Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263
Output data Year: 2018, Volume: 83, Number: 18, Pages: 11057-11066 Pages count : 10 DOI: 10.1021/acs.joc.8b01652
Authors Kokuev Aleksandr O. 1,2 , Antonova Yulia A. 1,3 , Dorokhov Valentin S. 1,2 , Golovanov Ivan S. 1 , Nelyubina Yulia V. 4 , Tabolin Andrey A. 1 , Sukhorukov Alexey Yu. 1 , Ioffe Sema L. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991, Moscow, Russian Federation
2 Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047, Moscow, Russian Federation
3 Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1, 119991, Moscow, Russian Federation
4 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991, Moscow, Russian Federation

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.
Cite: Kokuev A.O. , Antonova Y.A. , Dorokhov V.S. , Golovanov I.S. , Nelyubina Y.V. , Tabolin A.A. , Sukhorukov A.Y. , Ioffe S.L.
Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy,N-oxyenamines
Journal of Organic Chemistry. 2018. V.83. N18. P.11057-11066. DOI: 10.1021/acs.joc.8b01652 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000445713000036
Scopus: 2-s2.0-85052302958
OpenAlex: W2886825468
Citing:
DB Citing
OpenAlex 25
Scopus 26
Web of science 23
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