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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| Related URLs: | |
| 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 |
| Item ID: | 18869 |
| Date Deposited: | 16 Dec 2005 |
| Last Modified: | 02 Mar 2012 12:45 |
| Contributors: | Andrew, R. J. (Author) Mellor, J. M. (Author) |
| Date: | 8 September 2000 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/18869 |
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