Kinetic studies on sec-alcohol racemization with dicarbonylchloro(pentabenzylcyclopentadienyl)- and dicarbonylchloro(pentaphenylcyclopentadienyl)ruthenium catalysts

Denys Mavrynsky, Dmitry Murzin, Reko Leino

    Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

    5 Citeringar (Scopus)

    Sammanfattning

    Pentasubstituted cyclopentadienyl complexes of ruthenium R5CpRu(CO)(2)Cl (R=Ph, benzyl) form, upon activation with tBuOK, highly active catalysts for racemization of chiral sec-alcohols. In combination with suitable resolving enzymes, such catalyst systems can efficiently be utilized for dynamic kinetic resolution reactions providing chiral alcohols, after hydrolysis of the corresponding acetates, in high yields and high enantiomeric purities. Here, three such ruthenium complexes were first characterized by NMR spectroscopy and cyclic voltammetry analysis (CVA) for elucidating their electronic characteristics in detail. 5CpRu(CO)(2)Cl (Bn=benzyl) racemizes electron-rich substrates more efficiently and in most cases faster than its pentaphenyl substituted analogue, formerly often considered as the leading catalyst candidate for dynamic kinetic resolution applications. 5CpRu(CO)(2)Cl, in turn, is more efficient for electron-poor substrates.
    OriginalspråkOdefinierat/okänt
    Sidor (från-till)2436–2445
    Antal sidor10
    TidskriftChemCatChem
    Volym5
    Utgåva8
    DOI
    StatusPublicerad - 2013
    MoE-publikationstypA1 Tidskriftsartikel-refererad

    Nyckelord

    • alcohols
    • cyclopentadienyl ligands
    • kinetics
    • racemization
    • ruthenium

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