42812-82-8Relevant academic research and scientific papers
Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy
Ushakov, Pavel Yu.,Khatuntseva, Elizaveta A.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.,Sukhorukov, Alexey Yu.
, p. 5322 - 5327 (2019/11/13)
A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N?O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated. (Figure presented.).
