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EnglishTreatment 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
| Titolo: | Competitive Formation of β-Enaminones and 3-Amino-2(5H)-Furanones from the Isoxazolidine System: A Combined Synthetic and Quantum Chemical Study |
| Autori: | |
| Data di pubblicazione: | 2010 |
| Rivista: | |
| 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 effects |
| Handle: | http://hdl.handle.net/11570/1905988 |
| Appare nelle tipologie: | 14.a.1 Articolo su rivista |
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