Nos tutelles

CNRS

Rechercher





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

Publications

publié le , mis à jour le

2020



  • B. Doistau, L. Benda, J. - L. Cantin, O. Cador, F. Pointillart, W. Wernsdorfer, L. - M. Chamoreau, V. Marvaud, B. Hasenknopf, et G. Vives, « Dual switchable molecular tweezers incorporating anisotropic MnIII–salphen complexes », Dalton Transactions, vol. 49, nᵒ 26, p. 8872-8882, juill. 2020.
    Résumé : An alternative strategy for the synthesis of terpyridine based switchable molecular tweezers has been developed to incorporate anisotropic Mn(III)–salphen complexes. The free ligand was synthesized using a building block strategy based on Sonogashira coupling reactions and was then selectively metalated with manganese in a last step. The conformation of the tweezers was switched from an open ‘W’ shaped form to a closed ‘U’ form by Zn(II) coordination to the terpyridine unit bringing the two Mn–salphen moieties in close spatial proximity as confirmed by X-ray crystallography. An alternate switching mechanism was observed by the intercalation of a bridging cyanide ligand between the two Mn–salphen moieties that resulted in the closing of the tweezers. These dual stimuli are attractive for achieving multiple controls of the mechanical motion of the tweezers. A crystallographic structure of unexpected partially oxidized closed tweezers was also obtained. One of the two Mn–salphen moieties underwent a ligand-centered oxidation of an imino to an amido group allowing an intramolecular Mn–Oamide–Mn linkage. The magnetic properties of the manganese(III) dimers were investigated to evaluate the magnetic exchange interaction and analyze the single molecule magnet behavior.
    Mots-clés : E-POM, GOBS, POLE 2, POLE 3.
    Pièce jointe Snapshot 876.4 ko (source)
    Pièce jointe Full Text PDF 4.2 Mo (source)


  • 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)

2019

2018

2017

0 | 50 | 100 | 150 | 200

--- Exporter la sélection au format