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Séminaire Chimie ED459

Glycochimie synthétique pour les sciences de la vie : contrôle de la sélectivité de quelques réactions par des sels de fer

Prof. Jean-Marie Beau (Membre de l’Institut Universitaire de France / Institut de Chimie Moléculaire et des Matériaux d’Orsay – ICMMO, UMR 8182 CNRS, Université Paris-Sud / Institut de Chimie des Substances Naturelles ICSN UPR 2301 CNRS, Gif-sur-Yvette)

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Le Jeudi 16 Mai 2013 à 13h45
UM2, salle de cours SC-25.01 (attention, lieu inhabituel)

(La conférence sera présentée en français)

Iron salts have recently attracted considerable attention as inexpensive and environmentally friendly agents in a wide range of selective processes in organic synthesis, [1] and their use as Lewis acid in carbohydrate chemistry is well-documented. We will report a few remarkable transformations induced by iron (III) salts as a Lewis acid either under stoechiometric or catalyticconditions. The results are very concise preparations of important glyco-constructs.

In connection with ongoing work at the interface of chemistry and biology, we will present :

– An unprecedented a one-pot cascade of transformations induced by iron(III)-chloride hexahydrate, including acetal removal / C-C double bond isomerization / cyclization to adihydropyran / oxazoline formation on chiral substrates derived from the threecomponent borono-Mannich Petasis reaction.[2]

– A regioselective one-pot protection of carbohydrates, optimized on D-glucopyranosides, by using stable iron(III) chloride hexahydrate a single catalyst in a single reaction vessel. [3] Different building blocks, displaying different protecting group patterns areobtained in a single flask by fine-tuning the reaction conditions. This approach circumvents thenecessity of carrying out the time-consuming isolation and purification of intermediates.

– The use of catalytic amounts of Fe(III) triflate solvate for the efficient activation of the readily available the β-penta acetate of N-acetyl glucosamine in the direct and highly selective synthesis ofthe important GlcNAc β-glycoside motifs. [4]

References

1. Selected reviews : a) C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217 ; b) D. Diaz, P. Miranda, J. Padrón, V. Martín, Curr. Org. Chem. 2006, 10, 457 ; c) D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500 ; d) E. B. Bauer, Curr. Org. Chem. 2008, 12, 1341.
2. J.-F. Soulé, A. Mathieu, S. Norsikian, J.-M. Beau, Org. Lett. 2010, 12, 5322-5325.
3. Y. Bourdreux, A. Lemétais, D. Urban, J.-M. Beau, Chem. Comm. 2011, 47, 2146-2148.
4. A. Stévenin, F.-D. Boyer, J.-M. Beau, Eur. J. Org. Chem. 2012, 1699-1702.

Contact local IBMM : Pr. Alberto Marra (équipe Glycochimie)

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