Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers
Keyword(s):
We have previously clarified that the strongly electron-withdrawing CF3 group nicely affected the base-mediated proton shift of CF3-containing propargylic or allylic alcohols to afford the corresponding a,b-unsaturated or saturated ketones, respectively, which was applied this time to the Claisen rearrangement after O-allylation of the allylic alcohols with a CF3 group, followed by isomerization to the corresponding allyl vinyl ethers via the proton shift, enabling the desired rearrangement in a tandem fashion, or in a stepwise manner, the latter of which was proved to have attained an excellent diastereoselectivity with the aid of a palladium catalyst.
1975 ◽
Vol 40
(1)
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pp. 86-92
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2005 ◽
Vol 46
(16)
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pp. 2893-2896
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1992 ◽
Vol 33
(33)
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pp. 4735-4738
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