Catalytic asymmetric Henry reaction

被引:371
作者
Boruwa, Joshodeep [1 ]
Gogoi, Naminita [1 ]
Saikia, Partha Pratim [1 ]
Barua, Nabin C. [1 ]
机构
[1] CSIR, Nat Prod Chem Div, Reg Res Lab, Jorhat 785006, Assam, India
关键词
D O I
10.1016/j.tetasy.2006.12.005
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The classical Henry reaction, the coupling of a nitroalkane with a carbonyl compound in the presence of a base, is an important C-C bond forming reaction in organic chemistry giving beta-nitroalcohols, which are useful synthons in organic synthesis. However, an asymmetric version of the reaction, that has been developed recently, gives a new dimension to the classical Henry reaction whereby the control of stereochemistry of two newly generated carbon centres has become possible. In this review, the various catalytic methods for this purpose are discussed. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3315 / 3326
页数:12
相关论文
共 67 条
[21]  
Gogoi N, 2006, EUR J ORG CHEM, V2006, P1722, DOI [10.1002/ejoc.200500833, 10.1002/ejoe.200500833]
[22]  
HAJOS ZG, 1974, J ORG CHEM, V39, P1621
[23]  
HENRY LCR, 1895, CR HEBD ACAD SCI, V120, P265
[24]   Catalytic asymmetric nitroaldol reaction of alpha,alpha-difluoro aldehydes mediated by rare earth lithium BINOL complexes [J].
Iseki, K ;
Oishi, S ;
Sasai, H ;
Shibasaki, M .
TETRAHEDRON LETTERS, 1996, 37 (50) :9081-9084
[25]   Double catalytic activation with chiral Lewis acid and amine catalysts [J].
Kanemasa, S ;
Ito, K .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (23) :4741-4753
[26]   Enantioselective carbonyl-ene reaction of glyoxal derivatives catalyzed by cationic 3-oxobutylideneaminatocobalt(III) complexes [J].
Kezuka, S ;
Kogami, Y ;
Ikeno, T ;
Yamada, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (01) :49-58
[27]   Highly active 3-oxobutylideneaminatocobalt complex catalysts for an enantioselective hetero Diels-Alder reaction [J].
Kezuka, S ;
Mita, T ;
Ohtsuki, N ;
Ikeno, T ;
Yamada, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (07) :1333-1342
[28]   Enantioselective 1,3-dipolar cycloaddition reaction of nitrones with α,β-unsaturated aldehydes catalyzed by cationic 3-oxobutylideneaminatocobalt(III) complexes [J].
Kezuka, S ;
Ohtsuki, N ;
Mita, T ;
Kogami, Y ;
Ashizawa, T ;
Ikeno, T ;
Yamada, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (11) :2197-2207
[29]   Activation of nitroaldol reactions by diethylzinc and amino alcohols or diamines as promoters [J].
Klein, G ;
Pandiaraju, S ;
Reiser, O .
TETRAHEDRON LETTERS, 2002, 43 (42) :7503-7506
[30]   Enantioselective Henry reaction catalyzed by salen-cobalt complexes [J].
Kogami, Y ;
Nakajima, T ;
Ikeno, T ;
Yamada, T .
SYNTHESIS-STUTTGART, 2004, (12) :1947-1950