Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers

Autor:	Yoko Hamada, Rio Matsunaga, Tomoko Kawasaki-Takasuka, Takashi Yamazaki
Jazyk:	angličtina
Rok vydání:	2021
Předmět:	Claisen rearrangement isomerization trifluoromethyl Cieplak rule Organic chemistry QD241-441
Zdroj:	Molecules, Vol 26, Iss 14, p 4365 (2021)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules26144365
Popis:	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.
Databáze:	Directory of Open Access Journals
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