THE ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES IN AQUEOUS-MEDIA

被引:151
作者
KOBAYASHI, S
HACHIYA, I
机构
[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Shinjuku-ku, Tokyo, 162, Kagurazaka
关键词
ALDOL REACTION; LANTHANIDE TRIFLATE; AQUEOUS MEDIA; WATER SOLUBLE ALDEHYDE; SILYL ENOL ETHER;
D O I
10.1016/S0040-4039(00)91691-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aldol reaction of silyl enol ethers with aldehydes is successfully carried out in aqueous media by using a lanthanide trifluoromethanesulfonate as a catalyst. Water soluble aldehydes are applicable and the catalyst can be recovered and reused in this reaction.
引用
收藏
页码:1625 / 1628
页数:4
相关论文
共 13 条
[1]   ORGANOLANTHANIDE CATALYSIS OF A MUKAIYAMA ADDITION-REACTION [J].
GONG, L ;
STREITWIESER, A .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6235-6236
[2]   NEW APPLICATION OF SOLID ACID TO CARBON-CARBON BOND FORMATION REACTIONS - CLAY MONTMORILLONITE-CATALYZED ALDOL REACTIONS OF SILYL ENOL ETHERS WITH ALDEHYDES AND ACETALS [J].
KAWAI, M ;
ONAKA, M ;
IZUMI, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (04) :1237-1245
[3]   CLAY MONTMORILLONITE-CATALYZED ALDOL REACTIONS OF SILYL ENOL ETHERS WITH ALDEHYDES AND ACETALS [J].
KAWAI, M ;
ONAKA, M ;
IZUMI, Y .
CHEMISTRY LETTERS, 1986, (09) :1581-1584
[4]   TRITYL SALTS AS EFFICIENT CATALYSTS IN THE ALDOL REACTION [J].
KOBAYASHI, S ;
MURAKAMI, M ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1985, (10) :1535-1538
[6]   WATER-PROMOTED ORGANIC-REACTIONS - ALDOL REACTION OF SILYL ENOL ETHERS WITH CARBONYL-COMPOUNDS UNDER ATMOSPHERIC-PRESSURE AND NEUTRAL CONDITIONS [J].
LUBINEAU, A ;
MEYER, E .
TETRAHEDRON, 1988, 44 (19) :6065-6070
[7]   UNIQUE CATALYSIS BY EU(DPPM)3 - CATALYTIC MOLECULAR RECOGNITION IN ALDOL AND MICHAEL REACTIONS [J].
MIKAMI, K ;
TERADA, M ;
NAKAI, T .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5456-5459
[8]   NEW CROSS-ALDOL REACTIONS - REACTIONS OF SILYL ENOL ETHERS WITH CARBONYL-COMPOUNDS ACTIVATED BY TITANIUM TETRACHLORIDE [J].
MUKAIYAMA, T ;
BANNO, K ;
NARASAKA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (24) :7503-7509
[9]  
MUKAIYAMA T, 1982, ORG REACTIONS, V28, P203
[10]   FLUORIDE-ION CATALYZED ALDOL REACTION BETWEEN ENOL SILYL ETHERS AND CARBONYL-COMPOUNDS [J].
NAKAMURA, E ;
SHIMIZU, M ;
KUWAJIMA, I ;
SAKATA, J ;
YOKOYAMA, K ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :932-945