Transposition of allylic alcohols into carbonyl compounds mediated by transition metal complexes

被引：397
作者：
Uma, R [1 ]
Crévisy, C [1 ]
Grée, R [1 ]
机构：
[1] Ecole Natl Super Chim Rennes, Lab Synth & Activat Biomol, CNRS, UMR 6052, F-35700 Rennes, France
来源：
CHEMICAL REVIEWS | 2003年 / 103卷 / 01期
关键词：
D O I：
10.1021/cr0103165
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The isomerization of allylic alcohols to saturated carbonyls, mediated by homogeneous transition metal catalysts is studied. The conversion of allylic alcohols to saturated carbonyl compounds is a useful synthetic process and requires a two-step sequential oxidation and reduction reactions. A number of methods are developed harnessing the ability of transition metal complexes to migrate double bonds.
引用
收藏
页码：27 / 51
页数：25
相关论文
共 142 条
[1]   RHODIUM(I)-CATALYZED BIPHASIC ISOMERIZATION OF ALLYLIC ALCOHOLS [J].
ALPER, H ;
HACHEM, K .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11) :2269-2270
[2]   RUTHENIUM-CATALYZED ISOMERIZATION OF ALLYLIC ALCOHOLS TO SATURATED KETONES [J].
BACKVALL, JE ;
ANDREASSON, U .
TETRAHEDRON LETTERS, 1993, 34 (34) :5459-5462
[3]  
BAUDRY D, 1978, NOUV J CHIM, V2, P355
[4]   ISOMERIZATION OF ALLYL ETHERS CATALYZED BY CATIONIC IRIDIUM COMPLEX [IR(CYCLO-OCTA-1,5-DIENE)(PMEPH2)2]PF6 - HIGHLY STEREOSELECTIVE ROUTE TO TRANS-PROPENYL ETHERS [J].
BAUDRY, D ;
EPHRITIKHINE, M ;
FELKIN, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :694-695
[5]   A polymer-supported iridium catalyst for the stereoselective isomerisation of double bonds [J].
Baxendale, IR ;
Lee, AL ;
Ley, SV .
SYNLETT, 2002, (03) :516-518
[6]  
Bellemin-Laponnaz S, 1999, CHEM-EUR J, V5, P57, DOI 10.1002/(SICI)1521-3765(19990104)5:1<57::AID-CHEM57>3.0.CO
[7]  
2-B
[8]   Isomerization of allylic silyl ethers catalyzed by ReO3(OSiR3) complexes [J].
Bellemin-Laponnaz, S ;
Le Ny, JP ;
Osborn, JA .
TETRAHEDRON LETTERS, 2000, 41 (10) :1549-1552
[9]   Mechanistic insights into the very efficient [ReO3OSiR3]-catalyzed isomerization of allyl alcohols [J].
Bellemin-Laponnaz, S ;
Gisie, H ;
LeNy, JP ;
Osborn, JA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (09) :976-978
[10]   HOMOGENEOUS CATALYSIS - CATALYTIC PRODUCTION OF SIMPLE ENOLS [J].
BERGENS, SH ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :958-967
12345678910