Aromatic hydroxyl group-a hydrogen bonding activator in bifunctional asymmetric organocatalysis

被引:75
作者
Chauhan, Pankaj [1 ]
Chimni, Swapandeep Singh [1 ]
机构
[1] Guru Nanak Dev Univ, Dept Chem, UGC Ctr Adv Studies Chem, Amritsar 143005, Punjab, India
关键词
BAYLIS-HILLMAN REACTION; N-SULFONATED IMINES; METHYL VINYL KETONE; ENANTIOSELECTIVE CONJUGATE ADDITION; FRIEDEL-CRAFTS ALKYLATION; SUBSTITUTED ALPHA-CYANOACETATES; LEWIS-BASE ORGANOCATALYST; NON-BIARYL ATROPISOMERS; MICHAEL ADDITION; HILIMAN REACTION;
D O I
10.1039/c1ra00872b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Recent progress in asymmetric catalysis has contributed to the development of a diverse range of chiral organocatalysts that differ in their origin, structure and mode of activation. The bifunctional organocatalysts bearing aromatic hydroxyl (or phenolic) groups have emerged as a privileged class of organocatalyst. In these bifunctional organocatalysts, the aromatic hydroxyl group functions as a weak Bronsted acid or hydrogen bonding site and a nucleophilic or basic moiety such as amine and phosphine serve as a base or hydrogen bond acceptor. The bifunctional organocatalysts having these moieties have not been reviewed. In this review we are presenting the asymmetric transformations catalyzed by the bifunctional organocatalyst bearing an aromatic hydroxyl group.
引用
收藏
页码:737 / 758
页数:22
相关论文
共 203 条
[71]   Hydroxymethylation of α-substituted nitroacetates [J].
Ji, Cong-Bin ;
Liu, Yun-Lin ;
Cao, Zhong-Yan ;
Zhang, Yi-Yu ;
Zhou, Jian .
TETRAHEDRON LETTERS, 2011, 52 (46) :6118-6121
[72]   Organocatalytic asymmetric allylic alkylation of oxindoles with Morita-Baylis-Hillman carbonates [J].
Jiang, Kun ;
Peng, Jing ;
Cui, Hai-Lei ;
Chen, Ying-Chun .
CHEMICAL COMMUNICATIONS, 2009, (26) :3955-3957
[73]  
Jorgensen KAE, 2003, SYNTHESIS-STUTTGART, P1117
[74]   Chiral Bronsted Acids for Asymmetric Organocatalysis [J].
Kampen, Daniela ;
Reisinger, Corinna M. ;
List, Benjamin .
ASYMMETRIC ORGANOCATALYSIS, 2009, 291 :395-456
[75]   Design of chiral bifunctional secondary amine catalysts for asymmetric enamine catalysis [J].
Kano, Taichi ;
Maruoka, Keiji .
CHEMICAL COMMUNICATIONS, 2008, (43) :5465-5473
[76]   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
[77]   Hydrophobic amplification of noncovalent organocatalysis [J].
Kleiner, Christian M. ;
Schreiner, Peter R. .
CHEMICAL COMMUNICATIONS, 2006, (41) :4315-4317
[78]  
Langer P, 2000, ANGEW CHEM INT EDIT, V39, P3049, DOI 10.1002/1521-3773(20000901)39:17<3049::AID-ANIE3049>3.0.CO
[79]  
2-5
[80]   α,α-Diarylprolinols: bifunctional organocatalysts for asymmetric synthesis [J].
Lattanzi, Alessandra .
CHEMICAL COMMUNICATIONS, 2009, (12) :1452-1463