"Cofactor"-Controlled Enantioselective Catalysis

被引:99
作者
Dydio, Pawel [1 ]
Rubay, Christophe [1 ]
Gadzikwa, Tendai [1 ]
Lutz, Martin [2 ]
Reek, Joost N. H. [1 ]
机构
[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1098 XH Amsterdam, Netherlands
[2] Univ Utrecht, Bijvoet Ctr Biomol Res, NL-3584 CH Utrecht, Netherlands
关键词
SUPRAMOLECULAR CATALYSIS; SIGNAL AMPLIFICATION; BIDENTATE LIGANDS; HIGH-THROUGHPUT; TRANSITION; CHEMISTRY; MODELS; RECEPTORS; LIBRARIES; DESIGN;
D O I
10.1021/ja208589c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report an achiral bisphosphine rhodium complex with a binding site for the recognition of chiral anion guests. Upon binding small chiral guests-cofactors-the rhodium complex becomes chiral and can thus be used for asymmetric catalysis. Screening of a library of cofactors revealed that the best cofactors lead to hydrogenation catalysts that form the products with high enantioselectivity (ee's up to 99%). Interestingly, a competition experiment shows that even in a mixture of 12 cofactors high ee is obtained, indicating that the complex based on the best cofactor dominates the catalysis.
引用
收藏
页码:17176 / 17179
页数:4
相关论文
共 42 条
[1]   Supramolecular approaches to generate libraries of chelating bidentate ligands for homogeneous catalysis [J].
Breit, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (42) :6816-6825
[2]   Catalysts through self-assembly for combinatorial homogeneous catalysis [J].
Breit, Bernhard .
PURE AND APPLIED CHEMISTRY, 2008, 80 (05) :855-860
[3]   Singly Hydrogen Bonded Supramolecular Ligands for Highly Selective Rhodium-Catalyzed Hydrogenation Reactions [J].
Breuil, Pierre-Alain R. ;
Patureau, Frederic W. ;
Reek, Joost N. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2162-2165
[4]  
de Vries JG, 2003, EUR J ORG CHEM, V2003, P799
[5]  
Drauz K., 2002, ENZYME CATALYSIS ORG
[6]   Amide- and urea-functionalized pyrroles and benzopyrroles as synthetic, neutral anion receptors [J].
Dydio, Pawel ;
Lichosyt, Dawid ;
Jurczak, Janusz .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2971-2985
[7]   Remote Supramolecular Control of Catalyst Selectivity in the Hydroformylation of Alkenes [J].
Dydio, Pawel ;
Dzik, Wojciech I. ;
Lutz, Martin ;
de Bruin, Bas ;
Reek, Joost N. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :396-400
[8]   7,7′-Diureido-2,2′-diindolylmethanes: Anion Receptors Effective in a Highly Competitive Solvent, Methanol [J].
Dydio, Pawel ;
Zielinski, Tomasz ;
Jurczak, Janusz .
ORGANIC LETTERS, 2010, 12 (05) :1076-1078
[9]   Anion receptors based on 7,7′-diamido-2,2′-diindolylmethane [J].
Dydio, Pawel ;
Zielinski, Tomasz ;
Jurczak, Janusz .
CHEMICAL COMMUNICATIONS, 2009, (30) :4560-4562
[10]  
Fritsky IO, 2000, ANGEW CHEM INT EDIT, V39, P3255, DOI 10.1002/1521-3773(20000915)39:18<3255::AID-ANIE3255>3.0.CO