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

被引:45
作者
Andrew, RJ [1 ]
Mellor, JM [1 ]
机构
[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England
关键词
addition; Grignard reagents; organolithium; trifluoromethyl-ketones;
D O I
10.1016/S0040-4020(00)00597-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 alpha beta-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-alpha beta-unsaturated trifluoromethyl ketones as electrophilic partners. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7261 / 7266
页数:6
相关论文
共 45 条
[1]   Synthesis of trifluoromethylpyrroles and related heterocycles from 4-ethyloxy-1,1,1-trifluorobut-3-ene-2-one [J].
Andrew, RJ ;
Mellor, JM .
TETRAHEDRON, 2000, 56 (37) :7267-7272
[2]   Stereoselective synthesis of substituted bicyclo-[3.3.1]-nonan-9-ones by additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one [J].
Andrew, RJ ;
Mellor, JM ;
Reid, G .
TETRAHEDRON, 2000, 56 (37) :7255-7260
[3]  
Banks R.E., 1994, ORGANOFLUORINE CHEM
[4]   A stereoselective synthesis of (E)-alpha,beta-unsaturated ketones involving the reactions of organocerium reagents with secondary beta-enamino ketones [J].
Bartoli, G ;
Marcantoni, E ;
Petrini, M ;
Sambri, L .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (08) :913-918
[5]   HIGHLY STEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES BY CECL3 MEDIATED ADDITION OF GRIGNARD-REAGENTS TO BETA-ENAMINO KETONES [J].
BARTOLI, G ;
CIMARELLI, C ;
MARCANTONI, E ;
PALMIERI, G ;
PETRINI, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) :715-716
[6]   PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES [J].
BEGUE, JP ;
BONNETDELPON, D .
TETRAHEDRON, 1991, 47 (20-21) :3207-3258
[7]   Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: A probe of structural and conformational features contributing to inhibition [J].
Boger, DL ;
Sato, H ;
Lerner, AE ;
Austin, BJ ;
Patterson, JE ;
Patricelli, MP ;
Cravatt, BF .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (02) :265-270
[8]   Trifluoroacetonyl radicals: A versatile approach to trifluoromethyl ketones [J].
Denieul, MP ;
QuicletSire, B ;
Zard, SZ .
CHEMICAL COMMUNICATIONS, 1996, (22) :2511-2512
[9]   Trifluoromethyl-substituted imidazolines: Novel precursors of trifluoromethyl ketones amenable to peptide synthesis [J].
Derstine, CW ;
Smith, DN ;
Katzenellenbogen, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (35) :8485-8486
[10]   A STEREOSELECTIVE SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES INVOLVING THE REACTIONS OF ORGANOCUPRATES WITH BETA-ALKYLTHIO ALPHA,BETA-ENONES [J].
DIETER, RK ;
SILKS, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) :4687-4701