A remarkable rate acceleration of the Baylis-Hillman reaction

被引:54
作者
Lee, WD [1 ]
Yang, KS [1 ]
Chen, KM [1 ]
机构
[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan
关键词
D O I
10.1039/b103644k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of alpha -naphthyl acrylate with both aliphatic and aromatic aldehydes in the presence of DABCO (30 mol%) afforded the desired (alpha -methylene-beta -hydroxy)esters with reasonable chemical yields (51-88%) within 20 min.
引用
收藏
页码:1612 / 1613
页数:2
相关论文
共 21 条
[1]   Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications [J].
Aggarwal, VK ;
Mereu, A .
CHEMICAL COMMUNICATIONS, 1999, (22) :2311-2312
[2]   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
[3]   Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction [J].
Aggarwal, VK ;
Mereu, A ;
Tarver, GJ ;
McCague, R .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7183-7189
[4]   ACCELERATION IN WATER OF THE BAYLIS-HILLMAN REACTION [J].
AUGE, J ;
LUBIN, N ;
LUBINEAU, A .
TETRAHEDRON LETTERS, 1994, 35 (43) :7947-7948
[5]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[6]   The asymmetric Baylis-Hillman reaction [J].
Brzezinski, LJ ;
Rafel, S ;
Leahy, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4317-4318
[7]  
Ciganek E., 1997, ORG REACTIONS, V51, P201
[8]   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
[9]   THE BAYLIS-HILLMAN REACTION-MECHANISM AND APPLICATIONS REVISITED [J].
FORT, Y ;
BERTHE, MC ;
CAUBERE, P .
TETRAHEDRON, 1992, 48 (31) :6371-6384
[10]   MECHANISM OF ALPHA-SUBSTITUTION REACTIONS OF ACRYLIC DERIVATIVES [J].
HILL, JS ;
ISAACS, NS .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1990, 3 (05) :285-288