Trifluoromethane sulphonic acid: a Bronsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water

被引:46
作者
Loh, TP [1 ]
Xu, J [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 119260, Singapore
关键词
trifluoromethane sulphonic acid; allylation; aldehydes; water;
D O I
10.1016/S0040-4039(99)00122-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trifluoromethane sulphonic acid catalyses the addition of allyltributylstannane to carbonyl compounds in water to give the corresponding homoallylic alcohols in high yields. (C) 1999 Elsevier Science Ltd. AII rights reserved.
引用
收藏
页码:2431 / 2434
页数:4
相关论文
共 26 条
[1]  
CLUSKEY AM, 1997, TETRAHEDRON LETT, V38, P5217
[2]   PREPARATION OF AN OPTICALLY-ACTIVE PROSTAGLANDIN INTERMEDIATE VIA ASYMMETRIC INDUCTION [J].
COREY, EJ ;
ENSLEY, HE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) :6908-6909
[3]   STEREOCHEMICAL AND SPECTROSCOPIC STUDIES ON THE REACTION OF ALLYLSTANNANES WITH ALDEHYDES [J].
DENMARK, SE ;
WEBER, EJ ;
WILSON, TM ;
WILLSON, TM .
TETRAHEDRON, 1989, 45 (04) :1053-1065
[4]   CONVENIENT SYNTHESIS OF A HIGHLY EFFICIENT AND RECYCLABLE CHIRAL DIRECTOR FOR ASYMMETRIC INDUCTION [J].
ENSLEY, HE ;
PARNELL, CA ;
COREY, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (08) :1610-1612
[5]  
FLEMING I, 1991, CHEMTRACTS ORGANIC C, V4, P21
[6]   CYCLIC TRANSITION-STATE IN THE ACID-CATALYZED INTRAMOLECULAR ALLYLSTANNANE-ALDEHYDE CONDENSATION [J].
GEVORGYAN, V ;
KADOTA, I ;
YAMAMOTO, Y .
TETRAHEDRON LETTERS, 1993, 34 (08) :1313-1316
[7]   EFFECTS OF OLEFIN GEOMETRY ON THE STEREOCHEMISTRY OF LEWIS-ACID MEDIATED ADDITIONS OF CROTYLSTANNANES TO ALDEHYDES [J].
KECK, GE ;
SAVIN, KA ;
CRESSMAN, ENK ;
ABBOTT, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7889-7896
[8]   ORGANIC-REACTIONS IN AQUEOUS-MEDIA - WITH A FOCUS ON CARBON-CARBON BOND FORMATION [J].
LI, CJ .
CHEMICAL REVIEWS, 1993, 93 (06) :2023-2035
[9]   Indium-trichloride catalyzed Mukaiyama-aldol reaction in water: Solubility, aggregation and internal pressure effect [J].
Loh, TP ;
Pei, J ;
Koh, KSV ;
Cao, GQ ;
Li, XR .
TETRAHEDRON LETTERS, 1997, 38 (19) :3465-3468
[10]   Indium-trichloride catalyzed Michael reaction of silyl enol ethers with α,β-unsaturated carbonyl compounds under neat condition [J].
Loh, TP ;
Wei, LL .
TETRAHEDRON, 1998, 54 (26) :7615-7624