Polymer-supported silyl enol ethers. Synthesis and reactions with imines for the preparation of an amino alcohol library

被引:71
作者
Kobayashi, S
Hachiya, I
Suzuki, S
Moriwaki, M
机构
[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
基金
日本学术振兴会;
关键词
D O I
10.1016/0040-4039(96)00435-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polymer-supported silyl enol ethers (thioketene silyl acetals) were prepared from chloromethyl copoly-(styrene-1%-divinylbenzene) resin. The silyl enol ethers reacted with imines in the presence of a catalytic amount of scandium triflate (Sc(OTf)(3)) to afford beta-amino thioesters, which were reduced to amino alcohols in good yields. These reactions provide a convenient method for the preparation of an amino alcohol library. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2809 / 2812
页数:4
相关论文
共 30 条
[1]  
BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, V1, P85
[2]  
Colvin E. W., 1981, SILICON ORGANIC SYNT, P165
[3]  
FLEMING I, 1980, CHIMIA, V34, P265
[4]   APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS [J].
GORDON, EM ;
BARRETT, RW ;
DOWER, WJ ;
FODOR, SPA ;
GALLOP, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) :1385-1401
[5]   DIASTEREOSELECTION IN TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE CATALYZED REACTION OF SILYL KETENE ACETALS WITH IMINES [J].
GUANTI, G ;
NARISANO, E ;
BANFI, L .
TETRAHEDRON LETTERS, 1987, 28 (37) :4331-4334
[6]   CATALYTIC FRIEDEL-CRAFTS ACYLATION REACTIONS USING HAFNIUM TRIFLATE AS A CATALYST IN LITHIUM PERCHLORATE-NITROMETHANE [J].
HACHIYA, I ;
MORIWAKI, M ;
KOBAYASHI, S .
TETRAHEDRON LETTERS, 1995, 36 (03) :409-412
[7]   HAFNIUM(IV) TRIFLUOROMETHANESULFONATE, AN EFFICIENT CATALYST FOR THE FRIEDEL-CRAFTS ACYLATION AND ALKYLATION REACTIONS [J].
HACHIYA, I ;
MORIWAKI, M ;
KOBAYASHI, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (07) :2053-2060
[8]   AQUEOUS REACTIONS WITH A LEWIS-ACID AND AN ORGANOMETALLIC REAGENT - THE SCANDIUM TRIFLUOROMETHANESULFONATE-CATALYZED ALLYLATION REACTION OF CARBONYL-COMPOUNDS WITH TETRAALLYLTIN [J].
HACHIYA, I ;
KOBAYASHI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6958-6960
[9]  
ISHIHARA K, 1994, SYNLETT, P963
[10]  
KAWADA A, 1994, SYNLETT, P545