Studies towards total synthesis of antillatoxin:: Investigation of the indium-mediated allylation reactions of carbonyl compounds with β-bromocrotylbromide in water

被引:59
作者
Loh, TP [1 ]
Cao, GQ [1 ]
Pei, J [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 119260, Singapore
关键词
D O I
10.1016/S0040-4039(97)10826-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indium mediates the coupling of beta-bromocrotylbromide with carbonyl compounds in saturated ammonium chloride in the presence of lanthanide triflate under sonication to give the corresponding compounds in good yield and moderate to high syn diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1453 / 1456
页数:4
相关论文
共 15 条
[1]  
CASIRAGHI G, 1993, CHEMTRACTS ORG CHEM, V6, P336
[2]   SYNTHESIS OF KDO USING INDIUM-MEDIATED ALLYLATION OF 2,3/4,5-DI-O-ISOPROPYLIDENE-D-ARABINOSE IN AQUEOUS-MEDIA [J].
GAO, JM ;
HARTER, R ;
GORDON, DM ;
WHITESIDES, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3714-3715
[3]  
Ho D.S.-C., 1996, SYNLETT, P263
[4]  
ISAAC MB, 1995, TETRAHEDRON LETT, V36, P8957
[5]   TIN-MEDIATED AND INDIUM-MEDIATED ALLYLATION IN AQUEOUS-MEDIA - APPLICATION TO UNPROTECTED CARBOHYDRATES [J].
KIM, E ;
GORDON, DM ;
SCHMID, W ;
WHITESIDES, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5500-5507
[6]   HIGHLY EFFICIENT CARBONYL ALLYLATION OF 1,3-DICARBONYL COMPOUNDS IN AQUEOUS-MEDIUM [J].
LI, CJ ;
LU, YQ .
TETRAHEDRON LETTERS, 1995, 36 (16) :2721-2724
[7]   ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION [J].
LI, CJ .
CHEMICAL REVIEWS, 1993, 93 (06) :2023-2035
[8]   ORGANOMETALLIC REACTIONS IN AQUEOUS-MEDIA WITH INDIUM [J].
LI, CJ ;
CHAN, TH .
TETRAHEDRON LETTERS, 1991, 32 (48) :7017-7020
[9]  
Loh TP, 1997, MAIN GROUP MET CHEM, V20, P237
[10]  
LOH TP, UNPUB