Catalytic asymmetric carbon-carbon bond-forming reactions in aqueous media

被引:69
作者
Bhowmick, Sudipto [1 ]
Bhowmick, Kartick C. [1 ]
机构
[1] Visva Bharati Univ, Dept Chem, Div Organ Synth, Bolpur 731235, W Bengal, India
关键词
DIRECT ALDOL REACTION; ENANTIOSELECTIVE MICHAEL ADDITION; DIELS-ALDER REACTIONS; WATER-COMPATIBLE ORGANOCATALYSTS; MANNICH-TYPE REACTIONS; SMALL ORGANIC-MOLECULE; GALLIUM LEWIS-ACID; ARYLBORONIC ACIDS; HIGHLY EFFICIENT; ALPHA; BETA-UNSATURATED ALDEHYDES;
D O I
10.1016/j.tetasy.2011.11.009
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The development of enantioselective transformations has been the subject of numerous research efforts. In recent years, a variety of efficient asymmetric catalysts for different organic reactions in aqueous media have been introduced. This review summarizes an analysis of chiral metal complex reactions catalyzed as well as organocatalyzed reactions in aqueous media. The applications of a variety of chiral ligands alone, or in association with metal complexes, in water alone, as well as other conditions such as reactions in water in the presence of surfactants or in mixtures of water and organic solvents are described. Complete up to date results concerning asymmetric aldol reactions, 1,4-conjugate addition reactions, Mannich reactions, Diels-Alder reactions, Friedel-Craft reactions and so on have appeared in the literature. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1945 / 1979
页数:35
相关论文
共 212 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]   Friedel-Crafts-type alkylation in aqueous media using resin-supported peptide catalyst having polyleucine [J].
Akagawa, Kengo ;
Yamashita, Takuhiro ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
TETRAHEDRON LETTERS, 2009, 50 (40) :5602-5604
[3]   Asymmetric organocatalytic α-arylation of aldehydes [J].
Aleman, Jose ;
Cabrera, Silvia ;
Maerten, Eddy ;
Overgaard, Jacob ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5520-5523
[4]   Enantioselective organocatalytic aldol reaction of unactivated ketones with isatins [J].
Allu, Suresh ;
Molleti, Nagaraju ;
Panem, Ramachandrarao ;
Singh, Vinod K. .
TETRAHEDRON LETTERS, 2011, 52 (32) :4080-4083
[5]   Water versus Solvent-Free Conditions for the Enantioselective Inter- and Intramolecular Aldol Reaction Employing L-Prolinamides and L-Prolinethioamides as Organocatalysts [J].
Almasi, Diana ;
Alonso, Diego A. ;
Balaguer, Andrea-Nekane ;
Najera, Carmen .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (7-8) :1123-1131
[6]   Primary amine catalyzed direct asymmetric aldol reaction assisted by water [J].
Amedjkouh, M .
TETRAHEDRON-ASYMMETRY, 2005, 16 (08) :1411-1414
[7]   Asymmetric autocatalytic Mannich reaction in the presence of water and its implication in prebiotic chemistry [J].
Amedjkouh, Mohamed ;
Brandberg, Maria .
CHEMICAL COMMUNICATIONS, 2008, (26) :3043-3045
[8]   Aqua-organocatalyzed direct asymmetric aldol reaction with acyclic amino acids and organic bases with control of diastereo- and enantioselectivity [J].
Amedjkouh, Mohamed .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :390-395
[9]   Simple amphiphilic isosteviol-proline conjugates as chiral catalysts for the direct asymmetric aldol reaction in the presence of water [J].
An, Ya-Jie ;
Zhang, Yun-Xiao ;
Wu, Ya ;
Liu, Zhao-Min ;
Pi, Chao ;
Tao, Jing-Chao .
TETRAHEDRON-ASYMMETRY, 2010, 21 (06) :688-694
[10]   Water influences the enantioselectivity in the proline or prolinamide-catalyzed aldol addition of acetone to isatins [J].
Angelici, Gaetano ;
Correa, Rodrigo J. ;
Garden, Simon J. ;
Tomasini, Claudia .
TETRAHEDRON LETTERS, 2009, 50 (07) :814-817