Lithium perchlorate-accelerated Baylis-Hillman reactions

被引:121
作者
Kawamura, M
Kobayashi, S [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, CREST, Japan Sci & Technol Corp,Bunkyo Ku, Tokyo 1130033, Japan
[2] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1620825, Japan
关键词
D O I
10.1016/S0040-4039(98)02705-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The coupling of alpha,beta-unsaturated carbonyl compounds with aldehydes (the Baylis-Hillman reaction) was accelerated in the presence of a catalytic amount of 1,4-diazabicyclo[2,2,2]octane (DABCO) and lithium perchlorate in ether. A preliminary kinetic study revealed that the relative rate of the reaction using LiClO4 in ether was 8.0 x 10(2) times faster than that of the reaction without LiClO4. (C) 1999 Elsevier Science Ltd.
引用
收藏
页码:1539 / 1542
页数:4
相关论文
共 10 条
[1]   First-examples of metal and ligand accelerated catalysis of the Baylis-Hillman reaction [J].
Aggarwal, VK ;
Tarver, GJ ;
McCague, R .
CHEMICAL COMMUNICATIONS, 1996, (24) :2713-2714
[2]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[3]  
Baylis A. B, 1972, German Patent, Patent No. 2155113
[4]   SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].
DREWES, SE ;
ROOS, GHP .
TETRAHEDRON, 1988, 44 (15) :4653-4670
[5]   THE BAYLIS-HILLMAN REACTION-MECHANISM AND APPLICATIONS REVISITED [J].
FORT, Y ;
BERTHE, MC ;
CAUBERE, P .
TETRAHEDRON, 1992, 48 (31) :6371-6384
[6]   [1,3] SIGMATROPIC REARRANGEMENT OF ALLYL VINYL ETHERS AT AMBIENT-TEMPERATURE IN 3.0M LITHIUM PERCHLORATE-DIETHYL ETHER [J].
GRIECO, PA ;
CLARK, JD ;
JAGOE, CT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5488-5489
[7]   SYNTHESIS OF 2-(1-HYDROXYALKYL)ACRYLONITRILES BY THE COCATALYSIS OF A BASE AND AN ACID [J].
IMAGAWA, T ;
UEMURA, K ;
NAGAI, Z ;
KAWANISI, M .
SYNTHETIC COMMUNICATIONS, 1984, 14 (13) :1267-1273
[8]   The chalcogeno-Baylis-Hillman reaction: the first examples catalysed by chalcogenides in the presence of Lewis acids [J].
Kataoka, T ;
Iwama, T ;
Tsujiyama, S .
CHEMICAL COMMUNICATIONS, 1998, (02) :197-198
[9]   A TERTIARY PHOSPHINE-CATALYZED REACTION OF ACRYLIC COMPOUNDS WITH ALDEHYDES [J].
MORITA, K ;
SUZUKI, Z ;
HIROSE, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1968, 41 (11) :2815-+
[10]   A FACILE SYNTHESIS OF ALPHA-GLUCOSIDES AND ALPHA-RIBOSIDES FROM THE CORRESPONDING 1-O-ACYL SUGARS AND ALCOHOLS IN THE PRESENCE OF TRITYL PERCHLORATE [J].
MUKAIYAMA, T ;
KOBAYASHI, S ;
SHODA, S .
CHEMISTRY LETTERS, 1984, (06) :907-910