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Séminaire Chimie ED459

Asymmetric hydrogenation and transfer hydrogenation : an efficient approach to bio-relevant industrial targets

Dr. Tahar Ayad (équipe Catalyse, synthèse de biomolécules et développement durable, Laboratoire Charles Friedel, UMR 7223 CNRS, École Nationale Supérieure de Chimie de Paris / ChimieParisTech)

publié le

Le Jeudi 21 Mars 2013 à 13h45
UM2, salle de cours SC-16.01

The need for the production of high-quality products with minimum waste and energy demands is a key challenge in today’s environment.[1] In the present area of green chemistry, where environmentally benign reactions are required, asymmetric hydrogenation and transfer hydrogenation with its high yields, no byproducts, and very low catalyst loading is a key technology for the preparation of relevant pharmacologically active compounds.[2] Over the past few years, our group has been involved in the design and synthesis of new atropoisomeric ligands named SYNPHOS and DIFLUORPHOS for their use in asymmetric catalysis. Some applications of these ligands in asymmetric hydrogenation reactions for the syntheses of key synthetic precursors of biologically active products will be presented and discussed.[3]

References

1. a) Anastas, P. ; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301.
b) Horvath, I. ; Anastas, P. T. Chem. Rev. 2007, 107, 2167.

2. The Handbook of Homogeneous Hydrogenation ; de Vries, J. G., Elseiver, C. J., Eds. Wiley-VCH : Weinheim, Germany, 2007, vol. 1-3.

3. a) Tadaoka, H. ; Cartigny, D. ; Nagano, T. ; Gosavi, T. ; Ayad, T. ; Genet, J.-P. ; Ohshima, T. ; Ratovelomanana-Vidal, V. ; Mashima, K. Chem. Eur. J. 2009, 15, 9990.
b) Cartigny, D. ; Nagano, T. ; Ayad, T. ; Genet, J.-P. ; Ohshima, T. ; Mashima, K. ; Ratovelomanana-Vidal, V. Adv. Synth. Catal. 2010, 352, 1886.
c) Cartigny, D. ; Puntener, K. ; Ayad, T. ; Scalone, M. ; Ratovelomanana-Vidal, V. Org. Lett. 2010, 12, 3788.
d) Berhal, F. ; Esseiva, O. ; Martin, C.-H. ; Tone, H. ; Genet, J.-P. ; Ayad, T. ; Ratovelomanana-Vidal, V. Org. Lett. 2011, 13, 2806.
e) Wu, Z. ; Ayad, T. ; Ratovelomanana-Vidal, V. Org. Lett. 2011, 13, 3782.
f) Berhal, F. ; Wu, Z. ; Zhang, Z. ; Ayad, T. ; Ratovelomanana-Vidal, V. Org. Lett. 2012, 14, 3308.
g) Cartigny, D., Berhal, F. ; Nagano, T. ; Phansavath, P. ; Ayad, T. ; Genet, J.-P. ; Ohshima, T. ; Mashima, K. ; Ratovelomanana-Vidal, V. J. Org. Chem. 2012, 77, 4544.
h) Ma, X. ; Li, W. ; Li, X. ; Tao, X. ; Fan, W. ; Xie, X. ; Ayad, T. ; Ratovelomanana-Vidal, V. ; Zhang, Z. Chem. Commun. 2012, 48, 5352.
i) Cartigny, D. ; Berhal, F. ; Nagano, T. ; Phansavath, P. ; Ayad, T. ; Genet, J.-P. ; Ohshima, T. ; Mashima, K. ; Ratovelomanana-Vidal, V. J. Org. Chem. 2012, 77, 612.

Contact local IBMM : Dr. Thierry Durand

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