Gold-catalyzed rearrangement of substituted allyl aryl ethers

Ph 3PAuOTf catalyzes the rearrangement of substituted allyl aryl ethers via an ionic mechanism to produce both branched and linear products. Triphenylphosphinegold(I) complexes catalyze the Claisen-type rearrangement of aryl allyl ethers to the corresponding branched and linear products. The product...

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Bibliographic Details
Published in:Tetrahedron letters 2010-12, Vol.51 (50), p.6666-6669
Main Authors: Vyvyan, James R., Dimmitt, Heidi E., Griffith, Jennifer K., Steffens, Laura D., Swanson, Rebecca A.
Format: Article
Language:English
Subjects:
Aromatic compounds
Branched
Claisen rearrangement
Ethers
Gold catalysis
Lewis acid
Mitsunobu etherification
Olefins
Tetrahedrons
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Summary:Ph 3PAuOTf catalyzes the rearrangement of substituted allyl aryl ethers via an ionic mechanism to produce both branched and linear products. Triphenylphosphinegold(I) complexes catalyze the Claisen-type rearrangement of aryl allyl ethers to the corresponding branched and linear products. The product distribution depends on the olefin geometry of the allylic ether. Stereochemical transfer experiments support an ionic mechanism.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.10.078