Combinatorial ligand development based on mass spectrometric screening and a double mass-labeling strategy

Journal of the American Chemical Society

Volumn 130, Issue 11, 2008, Pages 3234-3235

  Markert, Christian ^a   Rösel, Pirmin ^a   Pfaltz, Andreas ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND;

ANALYTIC METHOD; ARTICLE; CATALYST; CHEMICAL LABELING; CHIRALITY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOMER; MASS SPECTROMETRY; METHODOLOGY; SCREENING; STRUCTURE ANALYSIS;

EID: 41449099289     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0740317     Document Type: Article

References (14)

1. (a) Archibald, B.; Brümmer, O.; Devenney, M.; Gorer, S.; Jandeleit, B.; Uno, T.; Weinberg, W. H.; Weskamp, T. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002; pp 885-990.
2. (b) Hoveyda, A. H. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds., Wiley-VCH: Weinheim, 2002; pp 991-1016.
3. Markert, C.; Pfaltz, A. Angew. Chem., Int. Ed. 2004, 43, 2498-2500.
4. Mass-labeled enantiomers have been used before for determining the enantiomeric purity of chiral products: (a) Horeau, A.; Nouaille, A. Tetrahedron Lett. 1990, 31, 2707-2710.
5. (b) Reetz, M. T.; Becker, M. H.; Klein, H. W.; Stöckigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758-1761.
6. (c) Yao, S.; Siuzdak, G.; Finn, M. G. J. Org. Chem. 2003, 68, 2540-2546.
7. (d) For a review on quasienatiomers, see: Zhang, Q.; Curran, D. P. Chem. - Eur. J. 2005, 11, 4866-4880 and references therein.
8. Reviews: (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, 1., Ed.; Wiley-VCH: New York, 2000: pp 593-649.
9. (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; pp 833-886.
10. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
11. Chen, P. Angew. Chem., Int. Ed. 2003, 42, 2832-2847.
12. B at low conversion when 1a/1b = 1. Thus samples were taken in the initial phase after ca. 1-2 turnovers.
13. Hilgraf, R.; Pfaltz, A. Adv. Synth. Catal. 2005, 347, 61-77.
14. rel of 45 was observed in the range 0-47% conversion. At higher conversion, the observed ee values no longer correlated with the catalyst intrinsic selectivity indicating slow catalyst decomposition or the onset of an unselective background reaction.