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.cook
qub.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
[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
