Determining the Enantioselectivity of Chiral Catalysts by Mass Spectrometric Screening of Their Racemic Forms

被引:51
作者
Ebner, Christian [1 ]
Mueller, Constanze A. [1 ]
Markert, Christian [1 ]
Pfaltz, Andreas [1 ]
机构
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
基金
瑞士国家科学基金会;
关键词
HOMOGENEOUS CATALYSIS; COMPLEXES; LIGANDS; CHEMISTRY; MIXTURES;
D O I
10.1021/ja111700e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselectivity of a chiral catalyst can be determined from its racemic form by mass spectrometric screening of a nonequal mixture of two mass-labeled quasienantiomeric substrates. The presented method opens up new possibilities for evaluating catalyst structures that are not readily available in enantiomerically pure form.
引用
收藏
页码:4710 / 4713
页数:4
相关论文
共 19 条
[1]   Mechanistic implications of pseudo zero order kinetics in kinetic resolutions [J].
Blackmond, Donna G. ;
Hodnett, Neil S. ;
Lloyd-Jones, Guy C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7450-7451
[2]  
de Vries JG, 2003, EUR J ORG CHEM, V2003, P799
[3]  
Dominguez B, 2001, ANGEW CHEM INT EDIT, V40, P4289, DOI 10.1002/1521-3773(20011119)40:22<4289::AID-ANIE4289>3.0.CO
[4]  
2-4
[5]   3,5-dialkyl effect on enantioselectivity in Pd chemistry: Applications involving both bidentate and monodentate auxiliaries [J].
Dotta, P ;
Kumar, PGA ;
Pregosin, PS ;
Albinati, A ;
Rizzato, S .
ORGANOMETALLICS, 2004, 23 (10) :2295-2304
[6]   Dialkyl effect on enantioselectivity:: π-stacking as a structural feature in P,N complexes of palladium(II) [J].
Dotta, P ;
Magistrato, A ;
Rothlisberger, U ;
Pregosin, PS ;
Albinati, A .
ORGANOMETALLICS, 2002, 21 (14) :3033-3041
[8]   Applications of combinatorial methods in catalysis [J].
Hagemeyer, A ;
Jandeleit, B ;
Liu, YM ;
Poojary, DM ;
Turner, HW ;
Volpe, AF ;
Weinberg, WH .
APPLIED CATALYSIS A-GENERAL, 2001, 221 (1-2) :23-43
[9]  
KOCH G, 1995, RECL TRAV CHIM PAY B, V114, P206
[10]   Is it possible to estimate the enantioselectivity of a chiral catalyst from its racemic mixture? [J].
Lagasse, F ;
Tsukamoto, M ;
Welch, CJ ;
Kagan, HB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (25) :7490-7491