A novel rearrangement pathway of 3-alkoxycarbonyl-4-carbamoylisoxazolidines, leading to 1H-pyrrole-2,5-diones by treatment with TBAF, is reported. DFT quantum chemical calculations support the reaction route, controlled by ring strain, which proceeds through the opening of a bicyclic intermediate, with aldehyde extrusion.
|Titolo:||Formation of 3-Aminofuran-2-(5H)-ones and 3-Amino-1H-pyrrole-2,5-diones by Rearrangement of Isoxazolidines|
|Data di pubblicazione:||2011|
|Appare nelle tipologie:||1.1 Articolo in rivista|