"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
[21]   Cavity-Tailored, Self-Sorting Supramolecular Catalytic Boxes for Selective Oxidation [J].
Lee, Suk Joong ;
Cho, So-Hye ;
Mulfort, Karen L. ;
Tiede, David M. ;
Hupp, Joseph T. ;
Nguyen, SonBinh T. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) :16828-+
[22]   Allosterically regulated supramolecular catalysis of acyl transfer reactions for signal amplification and detection of small molecules [J].
Masar, Martin S., III ;
Gianneschi, Nathan C. ;
Oliveri, Christopher G. ;
Stern, Charlotte L. ;
Nguyen, SonBinh T. ;
Mirkin, Chad A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (33) :10149-10158
[23]  
Meeuwissen J, 2010, NAT CHEM, V2, P615, DOI [10.1038/nchem.744, 10.1038/NCHEM.744]
[24]  
Merlau M.L., 2001, Angew. Chem. Int. Ed, V113, P4369
[25]   Recent progress in the design and synthesis of artificial enzymes [J].
Motherwell, WB ;
Bingham, MJ ;
Six, Y .
TETRAHEDRON, 2001, 57 (22) :4663-4686
[26]   Heteroligated Supramolecular Coordination Complexes Formed via the Halide-Induced Ligand Rearrangement Reaction [J].
Oliveri, Christopher G. ;
Ulmann, Pirmin A. ;
Wiester, Michael J. ;
Mirkin, Chad A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (12) :1618-1629
[28]   ALLOSTERIC EFFECTS IN ORGANIC-CHEMISTRY - SITE-SPECIFIC BINDING [J].
REBEK, J ;
TREND, JE ;
WATTLEY, RV ;
CHAKRAVORTI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (15) :4333-4337
[29]   Combinatorial transition-metal catalysis: Mixing monodentate ligands to control enantio-, diastereo-, and regioselectivity [J].
Reetz, Manfred T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) :2556-2588
[30]   Bidentate ligands by supramolecular chemistry - the future for catalysis? [J].
Sandee, Albertus J. ;
Reek, Joost N. H. .
DALTON TRANSACTIONS, 2006, (28) :3385-3391