A Bronsted acid and lewis base organocatalyst for the aza-Morita-Baylis-Hillman reaction

被引:120
作者
Matsui, K [1 ]
Takizawa, S [1 ]
Sasai, H [1 ]
机构
[1] Osaka Univ, ISIR, Ibaraki, Osaka 5670047, Japan
关键词
enantioselective aza-Morita-Baylis-Hillman reaction; bifunctional catalyst; Bronsted acid; Lewis base; organocatalysis;
D O I
10.1055/s-2006-933112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(S)-3-[2-(Diphenylphosphino)phenyl]BINOL has been established as an efficient asymmetric bifunctional organocatalyst for the aza-Morita-Baylis-Hillman (aza-MBH) reaction. The Bronsted acid and Lewis base functionalities cooperate in substrate activation to promote the reaction with high enantiocontrol.
引用
收藏
页码:761 / 765
页数:5
相关论文
共 36 条
[1]   Helical chirality control of palladium complexes that bear a tetrakis(phosphanyl)terphenyl ligand: Application as asymmetric Lewis acid catalysts [J].
Aikawa, K ;
Mikami, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5458-5461
[2]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[3]   Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction [J].
Balan, D ;
Adolfsson, H .
TETRAHEDRON LETTERS, 2003, 44 (12) :2521-2524
[4]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[5]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[6]  
Gröger H, 2001, CHEM-EUR J, V7, P5247
[7]   Dual catalyst control in the amino acid-peptide-catalyzed enantioselective Baylis-Hillman reaction [J].
Imbriglio, JE ;
Vasbinder, MM ;
Miller, SJ .
ORGANIC LETTERS, 2003, 5 (20) :3741-3743
[8]   A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions [J].
Ishii, T ;
Fujioka, S ;
Sekiguchi, Y ;
Kotsuki, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9558-9559
[9]   Power of cooperativity: Lewis acid-Lewis base bifunctional asymmetric catalysis [J].
Kanai, M ;
Kato, N ;
Ichikawa, E ;
Shibasaki, M .
SYNLETT, 2005, (10) :1491-1508
[10]   β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines [J].
Kawahara, S ;
Nakano, A ;
Esumi, T ;
Iwabuchi, Y ;
Hatakeyama, S .
ORGANIC LETTERS, 2003, 5 (17) :3103-3105