Synthesis of αβ-Unsaturated Trifluoromethyl Ketones from 4-Dimethylamino-1,1,1-trifluorobut-3-ene-2-one by Addition of Grignard Reagents

Enaminones are available by reaction of 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one with amines such as dimethylamine and they react with Grignard reagents to give αβ-unsaturated trifluoromethyl ketones in good yield by 1,4-addition followed by elimination. The generality of this procedure is contrasted...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 37; pp. 7261 - 7266
Main Authors Andrew, Rebecca J., Mellor, John M.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.09.2000
Subjects
addition
Grignard reagents
organolithium
trifluoromethylketones
Grignard reagents
organolithium
addition
trifluoromethylketones
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Summary:Enaminones are available by reaction of 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one with amines such as dimethylamine and they react with Grignard reagents to give αβ-unsaturated trifluoromethyl ketones in good yield by 1,4-addition followed by elimination. The generality of this procedure is contrasted with reactions based either on the use of organolithium nucleophiles, or the use of 4-alkoxy-αβ-unsaturated trifluoromethyl ketones as electrophilic partners.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00597-4