Hamada, Y.; Matsunaga, R.; Kawasaki-Takasuka, T.; Yamazaki, T. Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers. Molecules2021, 26, 4365.
Hamada, Y.; Matsunaga, R.; Kawasaki-Takasuka, T.; Yamazaki, T. Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers. Molecules 2021, 26, 4365.
We have previously clarified that the strongly electron-withdrawing CF3 group nicely affected the base-mediated proton migration reactions of CF3-containinig 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, followed by isomerization to the corresponding allyl vinyl ethers, enabling the desired rearrangement in a tandem fashion, or in a stepwise manner where a palladium catalyst attained an excellent diastereoselectivity.
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