使用β-取代的N-乙烯基恶唑烷酮的路易斯酸调控的面式立体发散性HDA反应
Lewis acid tuned facial stereodivergent HDA reactions using beta-substituted N-vinyloxazolidinones.
作者信息
Gohier Frédéric, Bouhadjera Keltoum, Faye Djibril, Gaulon Catherine, Maisonneuve Vincent, Dujardin Gilles, Dhal Robert
机构信息
UMR 6011 CNRS-Université du Maine, Laboratoire de Synthèse Organique (UCO2M), Faculté des sciences, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
出版信息
Org Lett. 2007 Jan 18;9(2):211-4. doi: 10.1021/ol062626l.
The [4 + 2] acido-catalyzed heterocycloaddition between new beta-substituted N-vinyl-1,3-oxazolidin-2-ones (with R' = Me, Ar, CH2 Ar) and beta,gamma-unsaturated alpha-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-alpha or endo-beta adducts. [reaction: see text].
新型β-取代的N-乙烯基-1,3-恶唑烷-2-酮（R' = 甲基、芳基、CH₂芳基）与β,γ-不饱和α-酮酯（R = 芳基）之间的[4 + 2]酸催化杂环加成反应得到了具有高内型和立体面选择性的杂环加合物。通过改变路易斯酸实现了立体面分化的完全反转，从而立体选择性地形成内型-α或内型-β加合物。[反应：见正文]
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