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Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers
Version 1
: Received: 21 June 2021 / Approved: 23 June 2021 / Online: 23 June 2021 (11:16:15 CEST)
A peer-reviewed article of this Preprint also exists.
Hamada, Y.; Matsunaga, R.; Kawasaki-Takasuka, T.; Yamazaki, T. Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers. Molecules 2021, 26, 4365. Hamada, Y.; Matsunaga, R.; Kawasaki-Takasuka, T.; Yamazaki, T. Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers. Molecules 2021, 26, 4365.
Abstract
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.
Keywords
Claisen rearrangement; isomerization; trifluoromethyl; Cieplak rule
Subject
Chemistry and Materials Science, Analytical Chemistry
Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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