Use of triazole-ring formation to attach a Ru/TsDPEN complex for asymmetric transfer hydrogenation to a soluble polymer

被引:18
作者
Zammit, Charlotte M. [1 ]
Wills, Martin [1 ]
机构
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
关键词
POLYETHYLENE-GLYCOL; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; RUTHENIUM(II) CATALYST; CLICK CHEMISTRY; KETONES; COMBINATION; BINDING; FUNCTIONALIZATION; ORGANOCATALYSTS; IMMOBILIZATION;
D O I
10.1016/j.tetasy.2013.05.022
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The cycloaddition of a chiral ligand containing a terminal alkyne to a soluble polymer containing an azide provides a convenient means for the attachment of an asymmetric transfer hydrogenation catalyst to a soluble polymer support. Using these ligands in complexes with Ru(II), gave good results in terms of conversion and enantioselectivity (up to 95% ee) in ketone reduction reactions. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:844 / 852
页数:9
相关论文
共 82 条
[1]   Polystyrene-Supported Diarylprolinol Ethers as Highly Efficient Organocatalysts for Michael-Type Reactions [J].
Alza, Esther ;
Sayalero, Sonia ;
Kasaplar, Pinar ;
Almasi, Diana ;
Pericas, Miquel A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (41) :11585-11595
[2]   A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].
Appukkuttan, P ;
Dehaen, W ;
Fokin, VV ;
Van der Eycken, E .
ORGANIC LETTERS, 2004, 6 (23) :4223-4225
[3]   A Solid-Supported Organocatalyst for Continuous-Flow Enantioselective Aldol Reactions [J].
Ayats, Carles ;
Henseler, Andrea H. ;
Pericas, Miquel A. .
CHEMSUSCHEM, 2012, 5 (02) :320-325
[4]   Enhancement of catalytic performance in asymmetric transfer hydrogenation by microenvironment engineering of the nanocage [J].
Bai, Shiyang ;
Yang, Hengquan ;
Wang, Peng ;
Gao, Jinsuo ;
Li, Bo ;
Yang, Qihua ;
Li, Can .
CHEMICAL COMMUNICATIONS, 2010, 46 (43) :8145-8147
[5]   UNIMOLECULAR AND BIMOLECULAR HOMOLYTIC REACTIONS OF ORGANOCHROMIUM AND ORGANOCOBALT COMPLEXES - KINETICS AND EQUILIBRIA [J].
BAKAC, A ;
ESPENSON, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (18) :5197-5202
[6]   A soluble-polymer system for the asymmetric transfer hydrogenation of ketones [J].
Bastin, S ;
Eaves, RJ ;
Edwards, CW ;
Ichihara, O ;
Whittaker, M ;
Wills, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5405-5412
[7]   High-Affinity Glycopolymer Binding to Human DC-SIGN and Disruption of DC-SIGN Interactions with HIV Envelope Glycoprotein [J].
Becer, C. Remzi ;
Gibson, Matthew I. ;
Geng, Jin ;
Ilyas, Rebecca ;
Wallis, Russell ;
Mitchell, Daniel A. ;
Haddleton, David M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15130-15132
[8]  
Bon SAF, 2001, MACROMOL SYMP, V165, P29, DOI 10.1002/1521-3900(200103)165:1<29::AID-MASY29>3.0.CO
[9]  
2-5
[10]   Origin of enantioselectivity in the Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones [J].
Brandt, P ;
Roth, P ;
Andersson, PG .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :4885-4890