Diels‐Alder between nitroalkenes derived from a sugar scaffold and cyclopentadiene were examined. Depending on chemical structure of nitroalkene and polarity of solvent used, the reaction proceeded via the formation of a nitronate intermediate. Cyclic nitronates highly functionalized were obtained as chemically stable and stereochemically pure compounds. [3,3] sigmatropic shift of these ones afforded the Diels Alder cycloadducts in quantitative yield. Mechanistic aspects of reaction between nitroalkenes and cyclopentadiene has been studied using DFT computational methods. Nitronate derivatives are attractive intermediates and open the way for the construction of valuable compounds with potential applications.

中文翻译：

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在杂-狄尔斯-桤木/[3,3]-Sigmatropic 重排途径中通过糖衍生的硝基烯烃生成环状硝基化合物。


对源自糖支架的硝基烯烃和环戊二烯之间的狄尔斯-阿尔德进行了检查。根据硝基烯烃的化学结构和所用溶剂的极性，反应通过形成硝基中间体进行。获得高度官能化的环状硝基化合物，作为化学稳定且立体化学纯的化合物。 [3,3] 这些化合物的 σ 位移提供了定量产率的 Diels Alder 环加合物。使用 DFT 计算方法研究了硝基烯烃和环戊二烯之间反应的机理。硝基衍生物是有吸引力的中间体，为构建具有潜在应用价值的化合物开辟了道路。