Design of novel polymer-supported chiral catalyst for asymmetric transfer hydrogenation in water

被引：66
作者：
Arakawa, Y [1 ]
Haraguchi, N [1 ]
Itsuno, S [1 ]
机构：
[1] Toyohashi Univ Technol, Dept Mat Sci, Toyohashi, Aichi 4418580, Japan
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 19期
关键词：
water; sulfonated polymer; polymer-support; chiral catalyst; asymmetric transfer hydrogenation;
D O I：
10.1016/j.tetlet.2006.03.041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New polymer-supported chiral sulfonamides containing sulfonated pendant group have been synthesized. Chiral catalyst prepared from the new polymer-support is more effective for asymmetric transfer hydrogenation of aromatic ketones in water compared to that prepared from conventional polystyrene-support. Polymer-supported catalysts containing quaternary ammonium salt as a pendant increased not only the reactivity but also the enantioselectivity in asymmetric transfer hydrogenation in water. Moreover, this type of polymer can be reused without loss of the catalytic activity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3239 / 3243
页数：5
相关论文
共 44 条
[1]   Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water [J].
Azoulay, S ;
Manabe, K ;
Kobayashi, S .
ORGANIC LETTERS, 2005, 7 (21) :4593-4595
[2]   Synthesis and evaluation of a chiral heterogeneous transfer hydrogenation catalyst [J].
Bayston, DJ ;
Travers, CB ;
Polywka, MEC .
TETRAHEDRON-ASYMMETRY, 1998, 9 (12) :2015-2018
[3]   Enantioselective catalysis in water: Mukaiyama-aldol condensation promoted by copper complexes of bisoxazolines supported on poly(ethylene glycol) [J].
Benaglia, M ;
Cinquini, M ;
Cozzi, F ;
Celentano, G .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (22) :3401-3407
[4]   Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation [J].
Bubert, C ;
Blacker, J ;
Brown, SM ;
Crosby, J ;
Fitzjohn, S ;
Muxworthy, JP ;
Thorpe, T ;
Williams, JMJ .
TETRAHEDRON LETTERS, 2001, 42 (24) :4037-4039
[5]   INTRODUCING TPPTS AND RELATED LIGANDS FOR INDUSTRIAL BIPHASIC PROCESSES [J].
CORNILS, B ;
KUNTZ, EG .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 502 (1-2) :177-186
[6]  
Cornils B., 2004, Aqueous-Phase Organometallic Catalysis: Concepts and Applications
[7]   Soluble polymers as scaffolds for recoverable catalysts and reagents [J].
Dickerson, TJ ;
Reed, NN ;
Janda, KD .
CHEMICAL REVIEWS, 2002, 102 (10) :3325-3343
[8]   Asymmetric catalysis by chiral lanthanide complexes in water [J].
Dickins, RS ;
Gaillard, S ;
Hughes, SP ;
Badari, A .
CHIRALITY, 2005, 17 (07) :357-363
[9]   Recoverable catalysts for asymmetric organic synthesis [J].
Fan, QH ;
Li, YM ;
Chan, ASC .
CHEMICAL REVIEWS, 2002, 102 (10) :3385-3465
[10]   Enantio- and diastereoselective, stereospecific Mannich-type reactions in water [J].
Hamada, T ;
Manabe, K ;
Kodayashi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7768-7769
12345