Treatment of 3-alkoxycarbonyl-4-acyl- or 3,4-dialkoxycarbonyl-substituted isoxazolidines with a mild base, such as tetrabutylammonium fluoride, affords beta-enaminones and/or 3-methylamino-2(5H)-furanones according to the nature of the substituents at C(4) and C(5). 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 beta-Enaminones and 3-Amino-2(5H)-furanones from the Isoxazolidine System: A Combined Synthetic and Quantum Chemical Study
RONSISVALLE, SIMONE;CHIACCHIO, MARIA ASSUNTA ROSSELLA;LANZA, GIUSEPPE;CHIACCHIO, Ugo
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 beta-enaminones and/or 3-methylamino-2(5H)-furanones according to the nature of the substituents at C(4) and C(5). 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.File in questo prodotto:
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