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Développements récents en dédoublement cinétique dynamique par hydrogénation asymétrique à l'aide de complexes de ruthénium(II) - synthèse de molécules bioactives

Céline Mordant
Abstract : This research work has dealt with the dynamic kinetic resolution (DKR) of various -substituted ß-keto esters via ruthenium-catalyzed asymmetric hydrogenation. An efficient access to anti -amino-ß-hydroxy-esters has been investigated based on the DKR of -amino-ß-keto ester hydrochlorides using [Ru(SYNPHOS)Br2] catalysts. This strategy of DKR via ruthenium-mediated hydrogenation has also been applied in the context of the total synthesis of Diltiazem and Taxotere's side-chain in order to prepare with high levels of diastereo- and enantioselectivity, anti -chloro-ß-hydroxy esters considered as the key intermediates. Moreover, the synthesis of Dolastatin 10 and its analogous has allowed us to develop the first efficient DKR of a -amino-ß-keto--methyl ester derived from (S)-proline and to point out the dramatic role of N-protecting groups on the diastereoselectivity of the hydrogenation reaction.
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Submitted on : Wednesday, March 2, 2005 - 8:00:00 AM
Last modification on : Wednesday, March 2, 2005 - 8:00:00 AM
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Céline Mordant. Développements récents en dédoublement cinétique dynamique par hydrogénation asymétrique à l'aide de complexes de ruthénium(II) - synthèse de molécules bioactives. Chemical Sciences. Chimie ParisTech, 2004. English. ⟨pastel-00001093⟩

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