Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers

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 α,β-unsaturated or saturated ketones, respectively, which was applied this time to the Claisen re...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2021-07, Vol.26 (14), p.4365
Main Authors: Hamada, Yoko, Matsunaga, Rio, Kawasaki-Takasuka, Tomoko, Yamazaki, Takashi
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Allyl compounds
Catalysts
Chemical reactions
Cieplak rule
Claisen rearrangement
Ethers
Isomerization
Ketones
Palladium
Stereoselectivity
trifluoromethyl
Vinyl ethers
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container_title Molecules (Basel, Switzerland)
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creator Hamada, Yoko
Matsunaga, Rio
Kawasaki-Takasuka, Tomoko
Yamazaki, Takashi
description 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 α,β-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.
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subjects Alcohol
Alcohols
Allyl compounds
Catalysts
Chemical reactions
Cieplak rule
Claisen rearrangement
Ethers
Isomerization
Ketones
Palladium
Stereoselectivity
trifluoromethyl
Vinyl ethers
title Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers
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