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Article

Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers

by
Yoko Hamada
,
Rio Matsunaga
,
Tomoko Kawasaki-Takasuka
and
Takashi Yamazaki
*
Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(14), 4365; https://doi.org/10.3390/molecules26144365
Submission received: 21 June 2021 / Revised: 5 July 2021 / Accepted: 14 July 2021 / Published: 19 July 2021
(This article belongs to the Special Issue Organofluorine Chemistry and Beyond)
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Abstract

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.
Keywords: Claisen rearrangement; isomerization; trifluoromethyl; Cieplak rule Claisen rearrangement; isomerization; trifluoromethyl; Cieplak rule
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MDPI and ACS Style

Hamada, Y.; Matsunaga, R.; Kawasaki-Takasuka, T.; Yamazaki, T. Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers. Molecules 2021, 26, 4365. https://doi.org/10.3390/molecules26144365

AMA Style

Hamada Y, Matsunaga R, Kawasaki-Takasuka T, Yamazaki T. Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers. Molecules. 2021; 26(14):4365. https://doi.org/10.3390/molecules26144365

Chicago/Turabian Style

Hamada, Yoko, Rio Matsunaga, Tomoko Kawasaki-Takasuka, and Takashi Yamazaki. 2021. "Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers" Molecules 26, no. 14: 4365. https://doi.org/10.3390/molecules26144365

APA Style

Hamada, Y., Matsunaga, R., Kawasaki-Takasuka, T., & Yamazaki, T. (2021). Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers. Molecules, 26(14), 4365. https://doi.org/10.3390/molecules26144365

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