从碳水化合物衍生构建块出发，经 Pudovik 和 Horner-Wadsworth-Emmons 反应，设计和合成新型 α-羟基 β-氟/β-三氟甲基和不饱和膦酸酯。

Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.

Centre for Advanced Technologies, Adam Mickiewicz University, Uniwersytetu Poznańskiego 10, 61-614 Poznań, Poland.

Molecules. 2022 Aug 24;27(17):5404. doi: 10.3390/molecules27175404.

Herein, we present the application of fluorinated carbohydrate-derived building blocks for α-hydroxy β-fluoro/β-trifluoromethyl and unsaturated phosphonates synthesis. Pudovik and Horner-Wadsworth-Emmons reactions were applied to achieve this goal. The proposed pathway of the key reactions is supported by the experimental results, as well as quantum chemical calculations. The structure of the products was established by spectroscopic (1D, 2D NMR) and spectrometric (MS) techniques. Based on our data received, we claim that the progress of the Pudovik and HWE reactions is significantly influenced by the acidic protons present in the molecules as assessed by pK values of the reagent.

在这里，我们展示了氟化碳水化合物砌块在α-羟基β-氟/β-三氟甲基和不饱和膦酸酯合成中的应用。应用了 Pudovik 和 Horner-Wadsworth-Emmons 反应来实现这一目标。关键反应的提出途径得到了实验结果和量子化学计算的支持。通过光谱（1D、2D NMR）和光谱（MS）技术确定了产物的结构。根据我们获得的数据，我们声称 Pudovik 和 HWE 反应的进展受到分子中存在的酸性质子的显著影响，这可以通过试剂的 pK 值来评估。