Stereoselective indium-mediated allylation of erythrulose derivatives in aqueous media

被引:19
作者
Carda, M [1 ]
Castillo, E
Rodriguez, S
Murga, J
Marco, JA
机构
[1] Univ Jaume 1, Dept Q Inorgan & Organ, E-12080 Castellon, Spain
[2] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain
关键词
D O I
10.1016/S0957-4166(98)00103-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A range of erythrulose derivatives has been allowed to react with allyl bromide and metallic indium in THF or aqueous THE Some of these allylations are highly stereoselective. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1117 / 1120
页数:4
相关论文
共 18 条
[1]   Stereochemistry and mechanism of the chemoselective allylation of alpha-substituted beta-keto esters with allyl bromide mediated by Zn in NH4Cl(aq)-THF [J].
Ahonen, M ;
Sjoholm, R .
ACTA CHEMICA SCANDINAVICA, 1997, 51 (6-7) :785-790
[2]   INDIUM-MEDIATED ALLYLATION OF ALDEHYDES - A CONVENIENT ROUTE TO 2-DEOXY AND 2,6-DIDEOXY CARBOHYDRATES [J].
BINDER, WH ;
PRENNER, RH ;
SCHMID, W .
TETRAHEDRON, 1994, 50 (03) :749-758
[3]  
Blomberg C., 1993, The Barbier reaction and related one-step processes
[4]   HIGHLY DIASTEREOSELECTIVE ADDITIONS OF ORGANOMETALLIC REAGENTS TO 1-O-SILYLATED 3,4-DI-O-BENZYL-L-ERYTHRULOSE DERIVATIVES [J].
CARDA, M ;
GONZALEZ, F ;
RODRIGUEZ, S ;
MARCO, JA .
TETRAHEDRON-ASYMMETRY, 1993, 4 (08) :1799-1802
[5]   DIASTEREOSELECTIVE SYNTHESIS OF ENANTIOMERIC TERTIARY ALCOHOLS VIA NUCLEOPHILIC ADDITIONS TO PROTECTED D-ERYTHRULOSE AND L-ERYTHRULOSE DERIVATIVES [J].
CARDA, M ;
GONZALEZ, F ;
RODRIGUEZ, S ;
MARCO, JA .
TETRAHEDRON-ASYMMETRY, 1992, 3 (12) :1511-1514
[6]   INDIUM-MEDIATED COUPLING OF ALPHA-(BROMOMETHYL)ACRYLIC ACID WITH CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA - CONCISE SYNTHESES OF (+)-3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID AND N-ACETYLNEURAMINIC ACID [J].
CHAN, TH ;
LEE, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4228-4232
[7]  
CINTAS P, 1995, SYNLETT, P1087
[8]  
Cintas P., 1993, ACTIVATED METALS ORG, P154
[9]   INDIUM-MEDIATED ALLYLATIONS OF UNPROTECTED CARBOHYDRATES IN AQUEOUS-MEDIA - A SHORT SYNTHESIS OF SIALIC-ACID [J].
GORDON, DM ;
WHITESIDES, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7937-7938
[10]   Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications [J].
Li, CJ .
TETRAHEDRON, 1996, 52 (16) :5643-5668