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Synthèse biomimétique de composés azotés biologiquement actifs

Abstract : This thesis work is devoted to the synthesis of biologically active nitrogen-containing compounds, particularly inspired by a biosynthetic reaction. Initially, our work aimed to develop a new pathway to α-amino acids using an enantioselective imine isomerization reaction. After various preliminary studies, the best precursors of α-amino acids that we have identified are α-keto amides. The 1,3 isomerization of an imine formed from an α-keto amide and diphenylmethanamine using various chiral alkoxides was then conducted. The alkoxide derived from (+)-N-methylpseudoephedrine, employed in sub-stoichiometric quantities, allowed obtaining the corresponding a-amino amide with 67% enantiomeric excess. It still remains to develop satisfactory operating conditions for the conversion of this adduct to an α-amino acid. The study of the 1,3 isomerization of imines allowed us to bring to light a 1,4 dehydrogenation reaction, which allows an original access to 2-azadienes and which requires the presence of oxygen. Thus, several non-activated 2-azadienes have been prepared by basic treatment of imines derived from acetophenones and diphenylmethanamine, under air atmosphere. In the last part, the study of the conjugate addition of a chiral oxazolidinone on dialkyl alkylidenemalonates was carried out, with the aim to develop a method of access to enantiopure β-amino acids. Reactions conditions developed allowed to obtain an excellent diastereoselectivity from most dialkyl alkylidenemalonates.
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Submitted on : Monday, June 25, 2012 - 3:11:21 PM
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  • HAL Id : tel-00711703, version 1


Julien Capra. Synthèse biomimétique de composés azotés biologiquement actifs. Chimie organique. Université Paris Sud - Paris XI, 2011. Français. ⟨tel-00711703⟩



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