133683-74-6Relevant articles and documents
Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines
Kokuev, Aleksandr O.,Antonova, Yulia A.,Dorokhov, Valentin S.,Golovanov, Ivan S.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Sukhorukov, Alexey Yu.,Ioffe, Sema L.
, p. 11057 - 11066 (2018)
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.
