59234-20-7Relevant academic research and scientific papers
Competitive formation of β-enaminones and 3-amino-2(5H)-furanones from the isoxazolidine system: A combined synthetic and quantum chemical study
Iannazzo, Daniela,Brunaccini, Elisa,Giofre, Salvatore V.,Piperno, Anna,Romeo, Giovanni,Ronsisvalle, Simone,Chiacchio, Maria A.,Lanza, Giuseppe,Chiacchio, Ugo
experimental part, p. 5897 - 5905 (2011/01/12)
Treatment of 3-alkoxycarbonyl-4-acyl- or 3,4-dialkoxycarbonyl-substituted isoxazolidines with a mild base, such as tetrabutylammonium fluoride, affords β-enaminones and/or 3-methylamino-2(5H)-furanones according to the nature of the substituents at C4 and C5. Two alternative mechanisms (lactonization and retro-aldolization) have been rationalized by DFT quantum chemical methods. Any realistic theoretical modeling requires the explicit inclusion of countercation and solvent effects. Substituted isoxazolidines afford β-enaminones and/or 3-methylamino-2(5H)-furanones by treatment with tetrabutylammonium fluoride according to the nature of the substituents at C4 and C5. Two alternative mechanisms (lactonization and retroaldolization) have been rationalized by DFT quantum chemical methods.
