COPPER-CATALYZED CONJUGATE ADDITION OF ORGANOMAGNESIUM REAGENTS TO ALPHA,BETA-ETHYLENIC ESTERS - A SIMPLE HIGH-YIELD PROCEDURE

被引：18

作者：

CAHIEZ, G

ALAMI, M

机构：

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(00)88506-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conjugate addition of organomagnesium reagents to alpha, beta-ethylenic esters is performed in THF, at room temperature (30 min to 1.5 h), in the presence of CuCl (3%) and Me3SiCl (1.2 eq.). Good yields of 1,4-addition products are obtained according to this very simple procedure.

引用

收藏

页码：7425 / 7428

页数：4

相关论文

共 13 条

[1] ORGANOCOPPER CONJUGATE ADDITION-REACTION IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].

ALEXAKIS, A ;

BERLAN, J ;

BESACE, Y .

TETRAHEDRON LETTERS, 1986, 27 (09) :1047-1050

[2] ORGANOMANGANESE(II) REAGENTS .18. COPPER-CATALYZED 1,4-ADDITION OF ORGANOMANGANESE CHLORIDE COMPOUNDS TO CONJUGATED ETHYLENIC ALDEHYDES [J].

CAHIEZ, G ;

ALAMI, M .

TETRAHEDRON LETTERS, 1989, 30 (52) :7365-7368

[3] ME3SICL/HMPA ACCELERATED CONJUGATE ADDITION OF CATALYTIC COPPER REAGENT - STEREOSELECTIVE SYNTHESIS OF ENOL SILYL ETHER OF ALDEHYDE [J].

HORIGUCHI, Y ;

MATSUZAWA, S ;

NAKAMURA, E ;

KUWAJIMA, I .

TETRAHEDRON LETTERS, 1986, 27 (34) :4025-4028

[4] REACTIONS INVOLVING ELECTRON-TRANSFER .3. CONJUGATE ADDITION OF LITHIUM DIMETHYLCUPRATE TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

HOUSE, HO ;

UMEN, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) :5495-&

[5]

KINTLARSEN T, 1963, ACTA CHEM SCAND, V17, P1426

[6] CONJUGATE ADDITION-REACTIONS OF ALPHA,BETA-UNSATURATED ESTERS WITH HIGHER-ORDER CUPRATES R2CU(CN)LI2 [J].

LIPSHUTZ, BH .

TETRAHEDRON LETTERS, 1983, 24 (02) :127-130

[7] MORE HIGHLY MIXED, HIGHER-ORDER CYANOCUPRATES RT(2-THIENYL)CU(CN)LI2 - EFFICIENT REAGENTS WHICH PROMOTE SELECTIVE LIGAND TRANSFER [J].

LIPSHUTZ, BH ;

KOZLOWSKI, JA ;

PARKER, DA ;

NGUYEN, SL ;

MCCARTHY, KE .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :437-447

[8]

MUNCHPET.J, 1966, B SOC CHIM FR, P471

[9] CONJUGATE ADDITIONS OF GRIGNARD REAGENTS TO ALPHA,BETA-UNSATURATED ESTERS [J].

MUNCHPETERSEN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (02) :170-176

[10] CONJUGATE ADDITIONS OF GRIGNARD REAGENTS TO ALPHA,BETA-UNSATURATED ESTERS .6. THE COURSE OF REACTIONS WITH ALLYLIC GRIGNARD REAGENTS [J].

MUNCHPETERSEN, J ;

JORGENSEN, PM ;

REFN, S .

ACTA CHEMICA SCANDINAVICA, 1959, 13 (10) :1955-1959