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

Research output: Contribution to journalArticlepeer-review

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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