Indium-mediated 2-oxonia cope rearrangement of 1,4-dienols to 1,3-dienols Natalie J. Capel Martin Lindley Gareth Pritchard Marc Kimber 2134/36715 https://repository.lboro.ac.uk/articles/journal_contribution/Indium-mediated_2-oxonia_cope_rearrangement_of_1_4-dienols_to_1_3-dienols/9390044 An indium-mediated isomerization of 1,4-dienols to 1,3-dienols is described. This procedure consists of the addition of pentadienylindium, in a protic solvent, to aldehydes giving the kinetic γ-allylation product in high yields. The subsequent conversion of this γ-allylation product to its thermodynamic 1,3-dienol α-isomer can be achieved by its exposure to indium triflate in the presence of a substoichiometric amount of aldehyde at room temperature. This transformation exhibited moderate to good substrate scope and has been shown to proceed by a 2-oxonia Cope rearrangement. 2019-01-30 16:00:30 Addition reaction Carbonyl compounds (organic) Catalysts Physical and chemical processes Medical and Health Sciences not elsewhere classified