Doctoral thesis (Dissertations and theses)
Novel Strategies towards aminophosphonic derivatives by [4+2] cycloadditions
Monbaliu, Jean-Christophe
2008
 

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Keywords :
Aminophosphonic derivatives; Diels–Alder cycloaddition; Asymmetric synthesis
Abstract :
[en] Aminophosphonic and related compounds were almost unknown 50 years ago, but today the literature data have considerably increased. Their negligible mammalian toxicity and their similarity with aminoacids confer on these compounds a top place as potential candidates for drugs. The discovery of numerous natural aminophosphonic derivatives endowed with biological properties useful to both medicinal and agricultural fields enhanced the infatuation for synthetic analogs and homologs. Intensive work has been performed towards alpha-aminophosphonic compounds, the direct analogs of natural alpha-aminoacids, disclosing versatile strategies, compatible both with molecular diversity and asymmetric synthesis. Less synthetic effort was devoted to the synthesis of higher homologs. Recent developments of the Diels-Alder reaction offer an asymmetric and convergent entry to various six-membered highly functionalizable key intermediates, compatible with molecular variety. As it is, the Diels-Alder (D-A) reaction should provide an original and versatile entry to beta-, gamma- and delta-aminophosphonic compounds, a challenging research area. As a direct consequence of the strategy, one of the two D-A partners (diene or dienophile) will act as vehicle for the phosphonate moiety. By contrast to its common use for the stabilization of alpha-negative charges, its implication in D-A reactions remains scarce. Indeed, the phosphonate moiety is not an efficient substituent susceptible to activate the D-A reaction; its use requires compensation by the activation of the other partner or by specific activation. Both synthetic organic and computational chemistry will furnish information to propose a fine understanding of the key D-A steps, in view to optimize the achievement of the corresponding cycloadducts. These cycloadducts will be considered as synth-/chirons for the synthesis of aminophosphonic compounds.
Disciplines :
Chemistry
Author, co-author :
Monbaliu, Jean-Christophe  ;  Université Catholique de Louvain – UCL > Institute of Condensed Matter and Nanosciences > Molecules, Solids and Reactivity (MOST)
Language :
English
Title :
Novel Strategies towards aminophosphonic derivatives by [4+2] cycloadditions
Defense date :
28 November 2008
Institution :
UCL - Université Catholique de Louvain
Degree :
PhD in Chemistry
Promotor :
Marchand-Brynaert, Jacqueline
Peeters, Daniel
President :
Gohy, Jean-François
Jury member :
Dive, Georges ;  Université de Liège - ULiège > Centres généraux > Centre d'ingénierie des protéines
Stevens, Christian
Riant, Olivier
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since 06 January 2014

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