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.
|Titolo:||Competitive Formation of beta-Enaminones and 3-Amino-2(5H)-furanones from the Isoxazolidine System: A Combined Synthetic and Quantum Chemical Study|
|Data di pubblicazione:||2010|
|Appare nelle tipologie:||1.1 Articolo in rivista|