N-(β,β-Difluorovinyl)oxazolidin-2-ones: First Synthesis and Application in [3+2]- and [4+2]-Cycloaddition-Type Reactions

T .B. Nguyen (1) , Arnaud Martel (1) , Robert Dhal (1) , Gilles Dujardin (1)

1 UCO2M - Unité de chimie organique moléculaire et macromoléculaire

N-(β,β-Difluorovinyl)oxazolidin-2-ones were conveniently prepared in good yields in two steps from the parent oxazolidin-2-ones. The [3+2]- and [4+2]-cycloaddition-type reactions with electron-deficient partners were investigated as first application of these new enamides. TMSOTf was efficient in promoting these two reactions, and the corresponding heterocyclic difluoro adducts were obtained in high yields.

Mots clés: N-(β; β-Difluorovinyl)oxazolidin-2-ones; trimethylsilyl trifluoromethanesulfonate; 3-dipolar cycloaddition; Diels-Alder reaction; dipolarophile; nitrone; heterodiene

Domaines: Chimie organique

T .B. Nguyen, Arnaud Martel, Robert Dhal, Gilles Dujardin. N-(β,β-Difluorovinyl)oxazolidin-2-ones: First Synthesis and Application in [3+2]- and [4+2]-Cycloaddition-Type Reactions. SYNLETT, 2009, 15, pp.2492-2496. ⟨10.1055/s-0029-1217744⟩. ⟨hal-00414347⟩