Asymmetric Induction by Chiral Borate Anions in Enantioselective Hydrogenation using a Racemic Rh-Binap Catalyst

被引:28
作者
Chen, Dianjun [1 ]
Sundararaju, Basker [1 ,2 ]
Krause, Rafael [1 ]
Klankermayer, Juergen [1 ]
Dixneuf, Pierre H. [2 ]
Leitner, Walter [1 ,3 ]
机构
[1] Rhein Westfal TH Aachen, Inst Tech & Makromol Chem, D-52074 Aachen, Germany
[2] Univ Rennes 1, CNRS, Inst Sci Chim, Lab Catalyse & Organomet,UMR 6226, F-35042 Rennes, France
[3] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
anions; asymmetric synthesis; homogenous catalysis; hydrogenation; ionic liquids; IONIC LIQUIDS; MECHANISM;
D O I
10.1002/cctc.200900229
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
With a little help from my friend: Combination of the racemic binap ligand with enantiopure bis-(S)-binol-borate anion results in enantioselectivities up to 57% ee in the rhodium-catalyzed asymmetric hydrogenation of dimethyl itaconate, which corresponds to 85% of the asymmetric induction caused by the enantiopure binap ligand. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:55 / 57
页数:3
相关论文
共 26 条
[1]   SUBSTRATE-INDUCED KINETIC RESOLUTION OF RACEMIC BIPHOSPHINES INSITU FOR HOMOGENEOUS CATALYSIS [J].
ALCOCK, NW ;
BROWN, JM ;
MADDOX, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (20) :1532-1534
[2]  
[Anonymous], 2008, ANGEW CHEM
[3]   Synthesis, properties and applications of BICAP: a new family of carbazole-based diphosphine Ligands [J].
Botman, PNM ;
Fraanje, J ;
Goubitz, K ;
Peschar, R ;
Verhoeven, JW ;
van Maarseveen, JH ;
Hiemstra, H .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (07) :743-754
[4]   Simple transformation of crystalline chiral natural anions to liquid medium and their use to induce chirality [J].
Branco, Luis C. ;
Gois, Pedro M. P. ;
Lourenco, Nuno M. T. ;
Kurteva, Vanya B. ;
Afonso, Carlos A. M. .
CHEMICAL COMMUNICATIONS, 2006, (22) :2371-2372
[5]   INTERMEDIATES IN THE ASYMMETRIC HYDROGENATION OF UNSATURATED CARBOXYLIC-ACID DERIVATIVES [J].
BROWN, JM ;
PARKER, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (08) :342-344
[6]   MECHANISM OF ASYMMETRIC HYDROGENATION - RHODIUM COMPLEXES FORMED BY UNSATURATED CARBOXYLIC-ACIDS, CARBOXYLATES, AND CARBOXAMIDES [J].
BROWN, JM ;
PARKER, D .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (14) :2722-2730
[7]   Towards phase-transfer catalysts with a chiral anion: inducing asymmetry in the reactions of cations [J].
Carter, C ;
Fletcher, S ;
Nelson, A .
TETRAHEDRON-ASYMMETRY, 2003, 14 (14) :1995-2004
[8]   Enantioselective hydrogenation with racemic and enantiopure binap in the presence of a chiral ionic liquid [J].
Chen, Dianjun ;
Schmitkamp, Mike ;
Francio, Giancarlo ;
Klankermayer, Juergen ;
Leitner, Walter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7339-7341
[9]   Chiral poisoning and asymmetric activation [J].
Faller, JW ;
Lavoie, AR ;
Parr, J .
CHEMICAL REVIEWS, 2003, 103 (08) :3345-3367
[10]  
GAUSEPOHL R, 2006, ANGEW CHEM, V118, P3772