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Unité de Formation et de Recherche de Chimie

Soutenance de la Thèse de Caleb Medena le 20 octobre 2017

Soutenance de la thèse de Caleb Medena le 20 octobre 2017

Intitulé :

" Synthèse d'hélicènes  énantioenrichis et application en catalyse    asymétrique "


New [6]helicene-based bisphosphinites were synthetized and used in asymmetric catalysis.Desired2,15-dimethoxy[6]helicenes were synthetized by two pathways: photochemical oxidative cyclization and CoI or RhI-catalyzed [2+2+2] cycloaddition. Both enantiomers of [6]Helixols were obtained by preparative chiral HPLC and/or using a chiral agent (up to 99.5 % ee).Even if desired helical cyclic scaffolds cannot be obtained due to the large distance between the two oxygen atoms. The synthesis of new [6]helicenes-based bisphosphinites were developed. Those last were used in gold-catalyzed enantioselective cycloisomerization of 1,6-enynes and Pd-catalyzed asymmetric allylic alkylation.

KEYWORDS: Helicenes – Chirality– Photocyclization – [2+2+2] Cycloaddition – Phosphinites – Ligand – Gold – Palladium – Homogenous asymmetric catalysis

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