Design and Synthesis of New α-hydroxy β-fluoro/β-trifluoromethyl and Unsaturated Phosphonates from Carbohydrate-Derived Building Blocks via Pudovik and Horner-Wadsworth-Emmons Reactions

Herein, we present the application of fluorinated carbohydrate-derived building blocks for alpha-hydroxy beta-fluoro/beta-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(a) values of the reagent.

Automated summary

In this study, we applied fluorinated carbohydrate-derived building blocks for the synthesis of alpha-hydroxy beta-fluoro/beta-trifluoromethyl and unsaturated phosphonates. Pudovik and Horner-Wadsworth-Emmons reactions were used to achieve this goal. The proposed pathway of the key reactions was supported by experimental results and quantum chemical calculations. The structures of the products were determined by spectroscopic and spectrometric techniques. Based on our findings, we conclude that the progress of the Pudovik and HWE reactions is influenced by acidic protons present in the molecules.