Investigation of the substrate influence on the fluorination with Deoxofluor of some highly functionalized alicyclic scaffolds

Nonn, Melinda and Fülöp, Ferenc and Kiss, Loránd (2018) Investigation of the substrate influence on the fluorination with Deoxofluor of some highly functionalized alicyclic scaffolds. Fluorine Notes (116). ISSN 2071-4807

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Abstract

Substrate influence on the fluorination of some highly functionalized alicyclic scaffolds with Deoxofluor has been investigated. The selected model compounds, hydroxylated, saturated and unsaturated six-memberd cyclic β-amino esters, have been synthesized from unsaturated cyclohexane β-amino acid stereoisomers through iodolactonization with stereo- and regiocontrol or stereoselective ring olefinic bond oxidation followed by regioselective oxirane opening. Depending on the stereostructure of the hydroxylated amino esters, their nucleophilic fluorination under various conditions afforded either the corresponding fluorine-containing substitution or elimination products.

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