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1-OXY-2,3-DIHYDRO-IMIDAZOL-4-ONES : INTERMEDIATES AND TARGETS AS WELL

Abstract : The present work deals with N-oxy-imidazolidinone type nitrones and the possible applications thereof. We developed an achiral nitrone, CYCNO, available in 3 stages from a glycine ester (66%) and a chiral nitrone, MiPNO. The latter was obtained in enantiopure form by a new optical resolution method; each enantiomer is accessible in 15 and 17% yield from the glycine ester. CYCNO was used as a model to study the reactivity of N-oxy-imidazolidinones toward aryl and heteroarylmagnesium halides, prepared by magnesium insertion or iodine-magnesium exchange. The reoxidation of the intermediate hydroxylamine led to a new family of nitrones, which may be used as spin traps. MiPNO was used for the preparation of unnatural amino acids, arylglycines and α-aryl,α-methylglycines. The sequence involves a totally diastereoselective addition of organomagnesium reagents. Seven arylglycine targets were prepared. In addition, 1,3-dipolar cycloaddition reactions between MiPNO and various alkenes led to isoxazolidines, in excellent regio- and diastereoselectivity. The cycloadduct can be converted into the corresponding α-amino-γ-lactone in a single operation, allowing the preparation of a new enantiopure γ-hydroxy-α-amino-acid.
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Submitted on : Friday, October 15, 2010 - 2:11:48 PM
Last modification on : Friday, November 6, 2020 - 4:05:48 AM
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  • HAL Id : tel-00526669, version 1

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CNRS | UJF | DCM | INC-CNRS | UGA

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Maryse Thiverny, Pierre Yves Chavant, Véronique Blandin. 1-OXY-2,3-DIHYDRO-IMIDAZOL-4-ONES : INTERMEDIATES AND TARGETS AS WELL. Autre. Université Joseph-Fourier - Grenoble I, 2010. Français. ⟨tel-00526669⟩

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