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|All Authors / Contributors:||
Angélique Jourdant; Jieping Zhu; Université de Paris-Sud.
|Notes:||Thèse : 2002PA112264.|
|Description:||231 p. ; 30 cm.|
|Responsibility:||Angélique Jourdant ; sous la dir. de Jieping Zhu.|
Chiral, non racemic piperidines such as (2R, 3,R) and (2R, 3S)-3-hydroxypipecolic acids are structural units found in many biologically and medicinally important natural and non natural products. Among 3-hydroxypiperidines, (-)-deoxoprosophylline is an alkaloid isolated from Prosopis Africana which possesses analgesic, anaesthetic and antibiotic activities. In the first part, we report new highly diastereoselective synthesis of these compounds based on the L-N,N-dibenzyl-(OTBDMS)-serinal recently developed in our laboratory. A stereoselective intramolecular reductive amination was used as a key cyclisation step. A macrocyclization method based on intramolecular SNAr reaction developed in our laboratory, has been employed in the synthesis of a many complex biologically important macrocycles with an endo aryl-aryl or aryl-alkyl ether linkage. As a continuation of our research program, we became interested in investigating the synthesis of macrocycles with an endo aryl-alkyl amine linkage. In the second part of this work, we describe an efficient synthesis of fourteen-members paracyclophanes, with or without chiral centre. These compounds have been tested as ligands in Ru(Il)-catalysed transfer hydrogenation. In the third part, in connection with our previous work, a general and efficient chemoselective hydrogenation of olefins with nitroaromatics using Wilkinson's catalyst has been developed.