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Étude de cycloisomérisations énantiosélectives d’énynes catalysées par des platinacycles carbéniques

Abstract : Enyne cycloisomerisations induce the formation of cyclic or polycyclic compounds from unsaturated substrates in a single step. These réactions catalysed by transition metals have a great interest in organic synthesis. However enantioselective versions of thèse reactions remain rare. Carbenic platinacycles with chiral monophosphines as ligands have been developped in our team. These complexes have been successfully used in the cycloisomerisation of allylpropargylamides into azabicyclo[4.1.0]heptenes ; enantiomeric excess up to 97% have been attained. This catalytic system has been extended to the desymetrisation of allylpropargylamides bearing a second vinyl moiety (ee’s up to 95%). These catalysts have been used also in the cycloisomerisation of 1,5-enynes bearing an oxygene fonstion at the propargylic position. Enantiomeric excess up to 75% have been obtained.
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Hélène Jullien. Étude de cycloisomérisations énantiosélectives d’énynes catalysées par des platinacycles carbéniques. Autre. Université Paris Sud - Paris XI, 2012. Français. ⟨NNT : 2012PA112320⟩. ⟨tel-00776100⟩

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