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

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 org...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2010-05, Vol.66 (19), p.3457-3462
Main Authors: Koldobskii, Andrey B., Tsvetkov, Nikolai P., Solodova, Ekaterina V., Verteletskii, Pavel V., Godovikov, Ivan A., Kalinin, Valery N.
Format: Article
Language:English
Subjects:
1,2- and 1,4-additions
Amination
Trifluoromethylenaminoketones
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.03.026