| Summary: | We have previously clarified that the strongly electron-withdrawing CF<sub>3</sub> group nicely affected the base-mediated proton shift of CF<sub>3</sub>-containing propargylic or allylic alcohols to afford the corresponding α,β-unsaturated or saturated ketones, respectively, which was applied this time to the Claisen rearrangement after <i>O</i>-allylation of the allylic alcohols with a CF<sub>3</sub> 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.
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