Synthesis of ?,?-unsaturated trifluoromethyl ketones from 4-dimethylamino-1,1,1-trifluorobut-3-ene-2-one by addition of Grignard reagents
Synthesis of ?,?-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 ?, ?-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-?, ?-unsaturated trifluoromethyl ketones as electrophilic partners.
addition, grignard reagents, organolithium, trifluoromethyl-ketones
alpha, beta-unsaturated ketones, stereoselective synthesis, efficientsynthesis, enamino ketones, (trifluoromethyl)trimethylsilane, condensation, inhibitors, methyl, esters
7261-7266
Andrew, R. J.
004eed6c-6a89-451a-9cd1-8e27ce59c9e4
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
8 September 2000
Andrew, R. J.
004eed6c-6a89-451a-9cd1-8e27ce59c9e4
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Andrew, R. J. and Mellor, J. M.
(2000)
Synthesis of ?,?-unsaturated trifluoromethyl ketones from 4-dimethylamino-1,1,1-trifluorobut-3-ene-2-one by addition of Grignard reagents.
Tetrahedron, 56 (37), .
(doi:10.1016/S0040-4020(00)00597-4).
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 ?, ?-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-?, ?-unsaturated trifluoromethyl ketones as electrophilic partners.
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Published date: 8 September 2000
Keywords:
addition, grignard reagents, organolithium, trifluoromethyl-ketones
alpha, beta-unsaturated ketones, stereoselective synthesis, efficientsynthesis, enamino ketones, (trifluoromethyl)trimethylsilane, condensation, inhibitors, methyl, esters
Identifiers
Local EPrints ID: 18869
URI: http://eprints.soton.ac.uk/id/eprint/18869
ISSN: 0040-4020
PURE UUID: c3f38059-3509-4592-b0df-07e0df2e947e
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Date deposited: 16 Dec 2005
Last modified: 15 Mar 2024 06:08
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Author:
R. J. Andrew
Author:
J. M. Mellor
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