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  • 1.
    Frölander, Anders
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Tilliet, Mélanie
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Lundgren, Stina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Levacher, Vincent
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Bifunctional Pybox Ligands: Application in Cyanations of BenzaldehydeManuscript (Other academic)
  • 2.
    Tilliet, Mélanie
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Synthesis and study of new oxazoline-based ligands2008Doctoral thesis, comprehensive summary (Other scientific)
    Abstract [en]

    This thesis deals with the study of oxazoline-based ligands in metal-catalyzed asymmetric reactions.

    The first part describes the synthesis of six new bifunctinal pyridine-bis(oxazoline) ligands and their applications in asymmetric metal-catalysis. These ligands, in addition to a Lewis acid coordination site, are equipped with a Lewis basic part in the 4-position of the oxazoline rings. Dual activation by means of this system was probed in cyanide addition to aldehydes.

    The second part is concerned with the synthesis of two pyridine-bis(oxazoline) ligands bearing bulky triazole groups in the 4-position of the oxazoline rings and a macrocyclic ligand consisting of a pyridine-bis(oxazoline) moiety and a diaza-18-crown-6 ether. The synthesis of these compounds benefits from the use of “click chemistry”. The ligands thus obtained were tested in different asymmetric catalytic reactions. Complexation studies with different bifunctional molecules that could bind into the cavity of the macrocycle were carried out using NMR spectroscopy.

    A third chapter is devoted to the synthesis of a supported pyridine-bis(oxazoline) catalyst and its use in catalysis. The pyridine-bis(oxazoline) ligand was efficiently connected to a polystyrene resin via a robust triazole linker. This resin could be employed in different metal-catalyzed asymmetric reactions and good results were obtained in terms of yield and enantioselectivity. Moreover, this polymer-bound ligand could be easily and efficiently recycled.

    Finally, the last part deals with the use of a hydroxy-containing phosphinooxazoline ligand in the hydrosilylation of imines and in the asymmetric intermolecular Heck reaction. A cationic iridium complex of this ligand was studied by NMR spectroscopy.

  • 3.
    Tilliet, Mélanie
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Frölander, Anders
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Levacher, Vincent
    UMR 6014 IRCOF, CNRS, Université et INSA de Rouen.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Convenient Preparation of Bifunctional Pybox Ligands2008In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 64, no 44, p. 10244-10249Article in journal (Refereed)
    Abstract [en]

     Starting from a common easily available pybox derivative, chiral ditopic ligands with pendant Lewis basic sites consisting of amine or phosphine oxide functions attached in the 4-positions of the oxazoline rings were prepared by simple synthetic procedures. From the same pybox derivative, a macrocyclic ligand containing a diaza-18-crown-6-ether ring linked via triazole groups was obtained employing 'click' chemistry.

  • 4.
    Tilliet, Mélanie
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Frölander, Anders
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Lundgren, Stina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Levacher, Vincent
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Evaluation of new pyridine-bis(oxazoline) ligands in asymmetric catalysisManuscript (Other academic)
  • 5.
    Tilliet, Mélanie
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Frölander, Anders
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Zetterberg, Krister
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Szabo, Zoltan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Influence of Ligand Secondary Interactions on Dynamic Processes in Alkene Ir ComplexesManuscript (Other academic)
  • 6.
    Tilliet, Mélanie
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Lundgren, Stina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Moberg, Christina
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Levacher, Vincent
    Laboratoire de Chimie Organique Fine et Hétérocyclique, UMR 6014, Université et INSA de Rouen.
    Polymer-Bound Pyridine-Bis(oxazoline). Preparation through Click Chemistry and Evaluation in Asymmetric Catalysis2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 13, p. 2079-2084Article in journal (Refereed)
    Abstract [en]

    A pyridine-bis(oxazoline) ligand was efficiently immobilized by copper(I)-catalyzed azide-alkyne cycloaddition onto a polystyrene resin. The so obtained click-pybox resin 1a was associated with various metal salts (YbCl3, LuCl3, CuOTf) and the resulting resin-bound catalysts were explored in ring-opening of cyclohexene oxide, silylcyanation of benzaldehyde and alkynylation of imines. These new polymer-supported catalysts exhibit good to excellent performances in terms of catalytic activity, enantioselectivity and recyclability.

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