Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

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.

Journal reference: Molecules 2021, 26, 4365
DOI: 10.3390/molecules26144365

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.

Subject Areas

Claisen rearrangement; isomerization; trifluoromethyl; Cieplak rule

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