1,3-Dipolar cycloaddition of N-substituted dipolarophiles and nitrones : highly efficient solvent-free reaction - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2008

1,3-Dipolar cycloaddition of N-substituted dipolarophiles and nitrones : highly efficient solvent-free reaction

Résumé

New isoxazolidines were synthesized in good to excellent yields by 1,3-dipolar cycloaddition of N-vinylamide dipolarophiles and nitrones. Strikingly, solvent-free conditions gave high conversion and yields, shortened reaction time, and minimized degradation products. N-Vinyloxazolidin-2-one and its analogues used in these cycloaddition reactions were conveniently prepared in excellent yields by a modified version of Buchwald's one-step copper-catalyzed vinylation using vinyl bromide. From the adducts, a two-step access to various unsymmetric aspartate derivatives was also described.

Domaines

Chimie organique

Dates et versions

hal-00280799 , version 1 (19-05-2008)

Identifiants

Citer

T .B. Nguyen, Arnaud Martel, Robert Dhal, Gilles Dujardin. 1,3-Dipolar cycloaddition of N-substituted dipolarophiles and nitrones : highly efficient solvent-free reaction. Journal of Organic Chemistry, 2008, 73 (7), pp.2621-2632. ⟨10.1021/jo702490w⟩. ⟨hal-00280799⟩

Collections

CNRS UNIV-LEMANS
34 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More