Lewis acid tuned facial stereodivergent HDA reactions using beta-sustituted N-vinyloxazolidinones - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2007

Lewis acid tuned facial stereodivergent HDA reactions using beta-sustituted N-vinyloxazolidinones

Résumé

The [4 + 2] acido-catalyzed heterocycloaddition between new β-substituted N-vinyl-1,3-oxazolidin-2-ones (with R‘ = Me, Ar, CH2 Ar) and β,γ-unsaturated α-ketoesters (R = Ar) afforded heteroadducts with high levels of endo and facial selectivities. A complete reversal of facial differentiation was achieved by varying the Lewis acid, leading to the stereoselective formation of either endo-α or endo-β adducts.

Domaines

Chimie organique
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Dates et versions

hal-00158404 , version 1 (28-06-2007)

Identifiants

Citer

Frédéric Gohier, Keltoum Bouhadjera, Djibril Faye, Catherine Gaulon-Nourry, Vincent Maisonneuve, et al.. Lewis acid tuned facial stereodivergent HDA reactions using beta-sustituted N-vinyloxazolidinones. Organic Letters, 2007, 9 (2), pp.211-214. ⟨10.1021/ol062626l⟩. ⟨hal-00158404⟩

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