Planar chiral pseudo-isocoumarins by copper catalysed desymmetrisation

Adam J. Wright, Fiona J. McMartin, Liam G. Dyer, Lloyd H. Sayer, Philip C. Bulman Page, G. Richard Stephenson

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    Abstract

    A new copper catalysed desymmetrisation reaction of bisalkynyl ferrocenecarboxylic acids results in the first asymmetric synthesis of planar chiral pseudo-isocoumarins in up to 64 % enantiomeric excess and up to 99 % yield. The absolute configuration of the chiral heterocycles is proven by chemical correlation and circular dichroism spectroscopy, opening the way for the rational extension of this method to produce bioactive isocoumarin-fused ferrocene derivatives.
    Original languageEnglish
    Article numbere202100841
    JournalEuropean Journal of Inorganic Chemistry
    Volume2022
    Issue number12
    Early online date7 Apr 2022
    DOIs
    Publication statusPublished - 27 Apr 2022

    Keywords

    • Asymmetric catalysis
    • Asymmetric synthesis
    • Chirality
    • Circular dichroism
    • Metallocenes

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