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  • 1.
    Hallman, Kristina
    et al.
    KTH, Superseded Departments, Chemistry.
    Frölander, Anders
    KTH, Superseded Departments, Chemistry.
    Wondimagegn, Tebikie
    KTH, Superseded Departments, Chemistry.
    Svensson, Mats
    KTH, Superseded Departments, Chemistry.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    OH–Pd(0) Interaction as a Stabilizing Factor in Palladium-Catalyzed Allylic Alkylations2004In: Proceedings of the National Academy of Sciences of the United States of America, ISSN 0027-8424, E-ISSN 1091-6490, Vol. 101, no 15, p. 5400-5404Article in journal (Refereed)
    Abstract [en]

    In palladium-catalyzed alkylations of allylic acetates with malonate as nucleophile, catalysts with oxazoline ligands bearing hydroxymethyl substituents in 4-position have been shown by density functional theory computations to undergo a conformational change on nucleophilic attack, which is accompanied by reduction of Pd(II) to Pd(0). The conformations of the Pd(0) complexes were shown to be governed by the presence of a hydrogen bond with the metal center acting as a hydrogen bond acceptor. The conformational change, which is absent in catalysts with O-alkylated analogs, largely affects the enantioselectivity of the catalytic process. This process is a previously uninvestigated example of where this type of weak hydrogen bond has been shown to influence the stereochemistry of a chemical reaction.

  • 2.
    Jönsson, Christina
    et al.
    KTH, Superseded Departments, Chemistry.
    Hallman, Kristina
    KTH, Superseded Departments, Chemistry.
    Andersson, Helene
    KTH, Superseded Departments, Signals, Sensors and Systems.
    Stemme, Göran
    KTH, Superseded Departments, Signals, Sensors and Systems.
    Malkoch, Michael
    KTH, Superseded Departments, Polymer Technology.
    Malmström, Eva
    KTH, Superseded Departments, Polymer Technology.
    Hult, Anders
    KTH, Superseded Departments, Polymer Technology.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Immobilized oxazoline-containing ligands in asymmetric catalysis - A review2002In: Bioorganic & Medicinal Chemistry Letters, ISSN 0960-894X, E-ISSN 1090-2120, Vol. 12, no 14, p. 1857-1861Article, review/survey (Refereed)
    Abstract [en]

    Metal complexes of chiral oxazoline derivatives immobilized on soluble as well as insoluble supports serve as versatile asymmetric catalysts in a variety of applications. In a few cases recovery and reuse of the chiral ligands have been achieved.

  • 3.
    Malkoch, Michael
    et al.
    KTH, Superseded Departments, Fibre and Polymer Technology.
    Hallman, Kristina
    KTH, Superseded Departments, Chemistry.
    Lutsenko, Serghey
    KTH, Superseded Departments, Chemistry.
    Hult, Anders
    KTH, Superseded Departments, Fibre and Polymer Technology.
    Malmström, Eva
    KTH, Superseded Departments, Fibre and Polymer Technology.
    Moberg, Christina
    KTH, Superseded Departments, Chemistry.
    Dendritic oxazoline ligands in enantioselective palladium-catalyzed allylic alkylations2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 23, p. 8197-8202Article in journal (Refereed)
    Abstract [en]

    First to fourth generation dendritic substituents based on 2,2-bis(hydroxymethyl)propionic acid and (1R,2S,5R)-menthoxyacetic acid were attached to 2-(hydroxymethyl)pyridinooxazoline and his[4-(hydroxymethyl)oxazoline] compounds. The new ligands obtained were assessed in palladium-catalyzed allylic alkylations. The first type of ligands exhibited enantioselectivity similar to that of a benzoyl ester derivative, whereas the latter type of ligands afforded products with higher selectivity than the analogous benzoyl ester. The activity of the dendritic catalysts decreased with increasing generation.

1 - 3 of 3
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