4.7 Article

Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of -, - and E-Lactones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 23, Pages 3857-3862

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600575

Keywords

gold catalysis; lactones; low catalyst loading; N-heterocyclic carbenes; solvent-free conditions

Funding

  1. ERC (FUNCAT)
  2. Umicore AG
  3. King Saud University
  4. University of St. Andrews

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The improved synthesis of -, - and E-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to - and -lactones in high regio- and stereoselectivity. Reactions were performed at low catalyst loadings and without the need for any additives. The use of a digold pre-catalyst provides a new synthetic route to functionalised E-lactones, poorly accessible using previous methodologies.

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