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

Autor:	Monika Bilska-Markowska, Wojciech Jankowski, Marcin Hoffmann, Marcin Kaźmierczak
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	fluorinated α-hydroxyphosphonates fluorinated unsaturated phosphonates fluorinated building blocks Pudovik Horner–Wadsworth–Emmons Organic chemistry QD241-441
Zdroj:	Molecules, Vol 27, Iss 17, p 5404 (2022)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules27175404
Popis:	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 pKa values of the reagent.
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/82c9f20f4f884560a3170e2f34ebdfd1 Zobrazit plný text záznamu View record in DOAJ Plný text ve formátu PDF Plný text ve formátu HTML
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