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
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 Vincenzo;PIPERNO, Anna;ROMEO, Giovanni;
2010-01-01
Abstract
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 effectsFile in questo prodotto:
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