Synthesis of α,β-unsaturated trifluoromethyl ketones from 4-dimethylamino-1,1,1-trifluorobut-3-ene-2-one by addition of Grignard reagents


Andrew, R. J. and Mellor, J. M. (2000) Synthesis of α,β-unsaturated trifluoromethyl ketones from 4-dimethylamino-1,1,1-trifluorobut-3-ene-2-one by addition of Grignard reagents. Tetrahedron, 56, (37), 7261-7266. (doi:10.1016/S0040-4020(00)00597-4).

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Description/Abstract

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 α, β-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-α, β-unsaturated trifluoromethyl ketones as electrophilic partners.

Item Type: Article
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Keywords: addition, grignard reagents, organolithium, trifluoromethyl-ketones alpha,beta-unsaturated ketones, stereoselective synthesis, efficientsynthesis, enamino ketones, (trifluoromethyl)trimethylsilane, condensation, inhibitors, methyl, esters
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 18869
Date Deposited: 16 Dec 2005
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/18869

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