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|Material Type:||Document, Thesis/dissertation, Internet resource|
|Document Type:||Internet Resource, Computer File|
|All Authors / Contributors:||
Cyrille Sabot; Charles Mioskowski; Université Louis Pasteur (Strasbourg).
|Notes:||Titre provenant de l'écran-titre.|
|Details:||AcceÌs : Internet.|
|Responsibility:||Cyrille Sabot ; [sous la direction de ] Charles Mioskowski.|
Amines bearing an adjacent enantiomerically pure chiral center are highly valuable in organic chemistry due to their extensive use as chiral auxiliaries, resolving agents and intermediates in the synthesis of biologically important molecules. The first part of the thesis deals with the kinetic resolution of a racemic mixture of amines with a chiral reagent Nacetylsulfonamide developed in the laboratory. This reagent affords enantioselective acetylation of a diamine of biological interest, the trans-2,5-diméthylpipérazine, with an enantiomeric excess of 86%. In addition, the use of achiral nitrogen-containing bases, together with the chiral N-acetylsulfonamide, could orchestrate the absolute stereochemical outcome of the kinetic resolution of amines. The second part of the thesis describes the development of a new catalytic system for the enantioselective acetylation of amines using bicyclic guanidines as catalyst. Finally, the third part highlights the catalytic activity of the bicyclic guanidine 1,5,7-triazabicyclo[4.4.0]dec-5-ene TBD for the aminolysis of esters and the deuteration of acidic molecules.