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
[1]   Invertible Enantioselectivity in 6′-Deoxy-6′-acylamino-β-isocupreidine-Catalyzed Asymmetric Aza-Morita-Baylis-Hillman Reaction: Key Role of Achiral Additive [J].
Abermil, Nacim ;
Masson, Geraldine ;
Zhu, Jeping .
ORGANIC LETTERS, 2009, 11 (20) :4648-4651
[2]  
Adair G, 2008, ALDRICHIM ACTA, V41, P31
[3]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[4]   Organocatalytic asymmetric conjugate additions [J].
Almasi, Diana ;
Alonso, Diego A. ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365
[5]   Synthetic applications of epoxide hydrolases [J].
Archelas, A ;
Furstoss, R .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2001, 5 (02) :112-119
[6]   The Rauhut-Currier reaction: a history and its synthetic application [J].
Aroyan, Carrie E. ;
Dermenci, Alpay ;
Miller, Scott J. .
TETRAHEDRON, 2009, 65 (21) :4069-4084
[7]  
AUSTIN JC, 1992, PROTEIN SCI, V1, P259
[8]   Recent developments in the asymmetric hydrolytic ring opening of epoxides catalysed by microbial epoxide hydrolase [J].
Bala, Neeraj ;
Chimni, Swapandeep Singh .
TETRAHEDRON-ASYMMETRY, 2010, 21 (24) :2879-2898
[9]   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
[10]   Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].
Ballini, R ;
Bosica, G ;
Fiorini, D ;
Palmieri, A ;
Petrini, M .
CHEMICAL REVIEWS, 2005, 105 (03) :933-971