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Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols

Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols Thumbnail


Abstract

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 ?-allylation product in high yields. The subsequent conversion of this ?-allylation product to its thermodynamic 1,3-dienol a-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.

Acceptance Date Dec 25, 2018
Publication Date Jan 9, 2019
Publicly Available Date Mar 28, 2024
Journal ACS Omega
Publisher American Chemical Society
Pages 785 -792
DOI https://doi.org/10.1021/acsomega.8b03118
Keywords Addition reaction; Carbonyl compounds (organic); Catalysts; Physical and chemical processes
Publisher URL https://doi.org/10.1021/acsomega.8b03118

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