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  • 1.
    Andersen, Sören M.
    et al.
    Novo Nordisk A/S, Denmark.
    Bollmark, Martin
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Substans och formulering.
    Berg, Robert
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Katalys.
    Fredriksson, Christofer
    Global Medicines Development, Sweden.
    Karlsson, Staffan
    AstraZeneca, Sweden.
    Liljeholm, Catarina
    Global Medicines Development, Sweden.
    Sörensen, Toft Henrik
    AstraZeneca, Sweden.
    A scalable route to 5-substituted 3-isoxazolol fibrinolysis inhibitor AZD65642014In: Organic Process Research & Development, ISSN 1083-6160, E-ISSN 1520-586X, Vol. 18, no 8, p. 952-959Article in journal (Refereed)
    Abstract [en]

    A practical and chromatography-free multikilogram synthesis of a 3-isoxazolol containing antifibrinolytic agent, AZD6564, has been developed in eight steps and 7% overall yield starting from methyl 2-chloroisonicotinate. Highlights in the synthesis are a Negishi coupling and an enzymatic resolution of a racemic ester. 

    Publisher's full text
  • 2.
    Lee, Taegyo
    et al.
    University of California, USA.
    Wilson, Tyler W.
    University of California, USA.
    Berg, Robert
    RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Katalys.
    Ryberg, Per
    RISE, SP – Sveriges Tekniska Forskningsinstitut.
    Hartwig, John F.
    University of California, USA.
    Rhodium-Catalyzed Enantioselective Silylation of Arene C–H Bonds: Desymmetrization of Diarylmethanols2015In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 137, no 21, p. 6742-6745Article in journal (Refereed)
    Abstract [en]

    We report a Rh-catalyzed, enantioselective silylation of arene C–H bonds directed by a (hydrido)silyl group. (Hydrido)silyl ethers that are formed in situ by hydrosilylation of benzophenone or its derivatives undergo asymmetric C–H silylation in high yield with excellent enantioselectivity in the presence of [Rh(cod)Cl]2 and a chiral bisphosphine ligand. The stereoselectivity of this process also allows enantioenriched diarylmethanols to react with site selectivity at one aryl group over the other. Enantioenriched benzoxasiloles from the silylation process undergo a range of transformations to form C–C, C–O, C–I, or C–Br bonds.

    Publisher's full text
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