Homogeneous asymmetric transfer hydrogenation of ketones using a ruthenium catalyst anchored on chitosan: natural chirality at work

被引:30
作者
Babin, Mathieu [1 ,2 ,3 ]
Clement, Roxanne [4 ]
Gagnon, Jonathan [1 ]
Fontaine, Frederic-Georges [2 ,3 ]
机构
[1] Univ Quebec, Dept Biol Chim & Geog, Rimouski, PQ G5L 3A1, Canada
[2] Univ Laval, Dept Chim, Quebec City, PQ G1V 0A6, Canada
[3] Univ Laval, Ctr Rech Proprietes Interfaces & Catalyse CERPIC, Quebec City, PQ G1V 0A6, Canada
[4] Univ Ottawa, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
COMPLEXES; LIGANDS; BEHAVIOR;
D O I
10.1039/c2nj40175d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A pivaloyl functionalized chitosan biopolymer was used as a polyligand for the [Ru(p-cymene)Cl-2] moiety. The functionalized biopolymer containing a metal to saccharide ratio of 0.33 was used as a catalyst for the asymmetric transfer hydrogenation of ketones. The reactions gave yields up to 80% and enantiomeric excesses up to 72%, with the intrinsic chirality of chitosan being the only source of enantioselection.
引用
收藏
页码:1548 / 1551
页数:4
相关论文
共 42 条
[1]   Regioselective pivaloylation of N-phthaloylchitosan: a promising soluble intermediate for chitosan chemistry [J].
Babin, Mathieu ;
Ruest, Amelie ;
Drouin, Guillaume ;
Sirois, Kathleen ;
Ouellet, Steeven ;
Gagnon, Jonathan .
CARBOHYDRATE RESEARCH, 2012, 351 :87-92
[2]   Recycling asymmetric hydrogenation catalysts by their immobilization onto ion-exchange resins [J].
Barbaro, Pierluigi .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (22) :5666-5675
[3]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[4]   Water-soluble arene ruthenium catalysts containing sulfonated diamine ligands for asymmetric transfer hydrogenation of α-aryl ketones and imines in aqueous solution [J].
Canivet, Jerome ;
Suess-Fink, Georg .
GREEN CHEMISTRY, 2007, 9 (04) :391-397
[5]  
Chirik P.J., 2010, CATALYSIS PRECIOUS M, P83
[6]   Ligands derived from carbohydrates for asymmetric catalysis [J].
Diéguez, M ;
Pàmies, OP ;
Claver, C .
CHEMICAL REVIEWS, 2004, 104 (06) :3189-3215
[7]   Self-supported chiral catalysts for heterogeneous enantioselective reactions [J].
Ding, Kuiling ;
Wang, Zheng ;
Shi, Lei .
PURE AND APPLIED CHEMISTRY, 2007, 79 (09) :1531-1540
[8]  
Everaere K, 2001, EUR J ORG CHEM, V2001, P275
[9]  
Hanessian S., 1983, Total Synthesis of Natural Products: TheChiron Approach
[10]   ASYMMETRIC TRANSFER HYDROGENATION OF AROMATIC KETONES CATALYZED BY CHIRAL RUTHENIUM(II) COMPLEXES [J].
HASHIGUCHI, S ;
FUJII, A ;
TAKEHARA, J ;
IKARIYA, T ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) :7562-7563