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Base-Mediated Cascade Rearrangements of Aryl-Substituted Diallyl Ethers

Jolene P. Reid, Catherine A. McAdam, Adam J. S. Johnston, Matthew N. Grayson, Jonathan M. Goodman and Matthew J. Cook*

*School of Chemistry and Chemical Engineering, Queen’s University Belfast, Belfast BT9 5AG, Northern Ireland, United Kingdom, Email: m.cookqub.ac.uk

J. P. Reid, C. A. McAdam, A. J. S. Johnston, M. N. Grayson, J. M. Goodman, M. J. Cook, J. Org. Chem., 2015, 80, 1472-1498.

DOI: 10.1021/jo502403n (free Supporting Information)


[2,3]-Wittig-Oxy-Cope

Isomerization-Claisen

[2,3]-Wittig-Oxy-Cope

Isomerization-Claisen

Abstract

Two base-mediated cascade rearrangement reactions of diallyl ethers lead to selective [2,3]-Wittig-oxy-Cope and isomerization-Claisen rearrangements. Both diaryl and arylsilyl-substituted 1,3-substituted propenyl substrates were examined, and each exhibits unique reactivity and different reaction pathways. The role of the base and solvent was key to the reactivity and selectivity observed.

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Key Words

[2,3]-Wittig Rearrangement, Oxy-Cope Rearrangement, Claisen Rearrangement


ID: J42-Y2015