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Accueil > Les équipes > Glycochimie Organique Biologique et Supramoléculaire (GOBS) > Publications

Publications

publié le , mis à jour le

2020



  • Z. Li, T. Bavaro, S. Tengattini, R. Bernardini, M. Mattei, F. Annunziata, R. B. Cole, C. Zheng, M. Sollogoub, L. Tamborini, M. Terreni, et Y. Zhang, « Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis », European Journal of Medicinal Chemistry, vol. 204, p. 112578, 2020.
    Mots-clés : CSOB, GOBS, POLE 3.


  • C. Tugny, N. del Rio, M. Koohgard, N. Vanthuyne, D. Lesage, K. Bijouard, P. Zhang, J. Meijide Suárez, S. Roland, E. Derat, O. Bistri-Aslanoff, M. Sollogoub, L. Fensterbank, et V. Mouriès-Mansuy, « β-Cyclodextrin–NHC–Gold(I) Complex (β-ICyD)AuCl: A Chiral Nanoreactor for Enantioselective and Substrate-Selective Alkoxycyclization Reactions », ACS Catalysis, vol. 10, nᵒ 11, p. 5964-5972, juin 2020.
    Résumé : NHC-capped β-cyclodextrin (β-ICyD) was used as a ligand for gold-catalyzed alkoxycyclization reactions. The cavity was found to be responsible for a triple selectivity: (i) the asymmetric shape of the cavity of β-ICyD induced highly stereoselective cyclizations, (ii) the shape of the interior favored the formation of a six-membered ring in the absence of a nucleophile, and finally, (iii) the encapsulation of the metal inside the cavity disfavored the addition of sterically hindered alcohols. Highly enantioselective and substrate-selective alkoxycyclizations of enynes are therefore promoted by the cavity-based molecular reactor (β-ICyD)AuCl.
    Mots-clés : CSOB, GOBS, MACO, POLE 1, POLE 3.
    Pièce jointe Full Text PDF 2.2 Mo (source)


  • G. Xu, S. Leloux, P. Zhang, J. M. Suárez, Y. Zhang, E. Derat, M. Ménand, O. Bistri‐Aslanoff, S. Roland, T. Leyssens, O. Riant, et M. Sollogoub, « Capturing the Monomeric (L)CuH in NHC-Capped Cyclodextrin: Cavity-Controlled Chemoselective Hydrosilylation of α,β-Unsaturated Ketones », Angewandte Chemie International Edition, vol. 59, nᵒ 19, p. 7591-7597, 2020.
    Résumé : The encapsulation of copper inside a cyclodextrin capped with an N-heterocyclic carbene (ICyD) allowed both to catch the elusive monomeric (L)CuH and a cavity-controlled chemoselective copper-catalyzed hydrosilylation of α,β-unsaturated ketones. Remarkably, (α-ICyD)CuCl promoted the 1,2-addition exclusively, while (β-ICyD)CuCl produced the fully reduced product. The chemoselectivity is controlled by the size of the cavity and weak interactions between the substrate and internal C−H bonds of the cyclodextrin.
    Mots-clés : cavities, copper hydride, cyclodextrins, GOBS, hydrosilylation, MACO, N-heterocyclic carbenes, POLE 1, POLE 3, α, β-unsaturated ketones.
    Pièce jointe Full Text PDF 3.2 Mo (source)

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