Synthesis of novel β-dialkylamino-α,β-unsaturated trifluoromethylketones containing cyclobutene fragment and their reactions with organolithium and Grignard reagents

• Published in: Tetrahedron Vol. 66; no. 19; pp. 3457 - 3462
• Main Authors: Koldobskii, Andrey B., Tsvetkov, Nikolai P., Solodova, Ekaterina V., Verteletskii, Pavel V., Godovikov, Ivan A., Kalinin, Valery N.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 08-05-2010; Elsevier
• Subjects: 1,2- and 1,4-additions; Amination; Trifluoromethylenaminoketones; Amination; 1,2- and 1,4-additions; Trifluoromethylenaminoketones
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.03.026

The highly reactive trifluoromethylenaminoketones, with a strained cyclobutene and norbornadiene moieties were firstly prepared from the corresponding β-halogeno-α,β-unsaturated trifluoromethylketones in almost quantitative yields. The ambident properties of these compounds in the reactions with organolithiums were discovered. The simple methods to control the selectivity of 1,2- or 1,4-addition of lithiated nucleophiles have been investigated.
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