APPLICATION OF INDIUM ATE COMPLEXES TO SYNTHETIC CHEMISTRY - SELECTIVE CONJUGATE ADDITION TO ENONES AND COUPLING WITH ALLYLIC HALIDES

被引:57
作者
ARAKI, S [1 ]
SHIMIZU, T [1 ]
JIN, SJ [1 ]
BUTSUGAN, Y [1 ]
机构
[1] NAGOYA INST TECHNOL,DEPT APPL CHEM,GOKISO CHO,SHOWA KU,NAGOYA,AICHI 466,JAPAN
关键词
D O I
10.1039/c39910000824
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tetraorganoindium ate complexes, prepared by the addition of organolithium reagents to trialkylindium, reacted with alpha,beta-unsaturated ketones in a 1,4-addition fashion; allylic indates derived from allylic indium sesquihalides coupled with allylic halides regio- and stereo-specifically to give high yields of head-to-tail 1,5-dienes.
引用
收藏
页码:824 / 825
页数:2
相关论文
共 17 条
[1]   CYCLOPROPANATION OF ELECTRON-DEFICIENT ALKENES AND WIDEQVIST-TYPE SYNTHESIS OF CYCLOPROPANES MEDIATED BY INDIUM METAL [J].
ARAKI, S ;
BUTSUGAN, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) :1286-1287
[2]   A BARBIER ALLYLATION AND A REFORMATSKY REACTION OF CARBONYL-COMPOUNDS MEDIATED BY INDIUM(I) IODIDE [J].
ARAKI, S ;
ITO, H ;
KATSUMURA, N ;
BUTSUGAN, Y .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 369 (03) :291-296
[3]   SYNTHESIS OF BETA-HYDROXYESTERS BY REFORMATSKY REACTION USING INDIUM METAL [J].
ARAKI, S ;
ITO, H ;
BUTSUGAN, Y .
SYNTHETIC COMMUNICATIONS, 1988, 18 (04) :453-458
[4]   PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS [J].
ARAKI, S ;
SHIMIZU, T ;
JOHAR, PS ;
JIN, SJ ;
BUTSUGAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2538-2542
[5]   INDIUM-INDUCED ALLYLATION OF ACID ANHYDRIDES - A FACILE SYNTHESIS OF ALLYLATED BUTENOLIDES AND PHTHALIDES [J].
ARAKI, S ;
KATSUMURA, N ;
ITO, H ;
BUTSUGAN, Y .
TETRAHEDRON LETTERS, 1989, 30 (12) :1581-1582
[6]   INDIUM IN ORGANIC-SYNTHESIS - INDIUM-MEDIATED ALLYLATION OF CARBONYL-COMPOUNDS [J].
ARAKI, S ;
ITO, H ;
BUTSUGAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1831-1833
[7]   REACTIVITY OF ALLYLIC ORGANOMETALLIC COMPOUNDS OF LITHIUM, SODIUM, MAGNESIUM, ZINC, CADMIUM AND ALUMINUM - RECENT ADVANCES [J].
COURTOIS, G ;
MIGINIAC, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 69 (01) :1-44
[8]  
HARTLEY FR, 1987, USE ORGANOMETALLIC C
[9]   SYNTHESIS OF ALKALINTETRAPHENYLINDATES AND CRYSTAL STRUCTURE OF NA(IN(C6H5)4) [J].
HOFFMANN, K ;
WEISS, E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 50 (01) :25-31
[10]   METAL-ALKYL COMPOUNDS .14. CRYSTAL STRUCTURES OF K(IN(CH3)4), RB(IN(CH3)4) AND CS(IN(CH3)4) [J].
HOFFMANN, K ;
WEISS, E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 50 (01) :17-24