Pattern-based recognition for determination of enantiomeric excess, using chiral auxiliary induced chemical shift perturbation NMR

Organic Letters

Volumn 12, Issue 11, 2010, Pages 2540-2543

  Lei, Xinxiang ^a,b   Liu, Lu ^a   Chen, Xiaojing ^a   Yu, Xiaochun ^a   Ding, Lisheng ^b   Zhang, Anjiang ^c  

^a WENZHOU UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

^c NINGBO INSTITUTE OF MATERIALS TECHNOLOGY AND ENGINEERING   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID;

ARTICLE; AUTOMATED PATTERN RECOGNITION; CHEMICAL STRUCTURE; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

CARBOXYLIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PATTERN RECOGNITION, AUTOMATED; STEREOISOMERISM;

EID: 77953019085     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100773s     Document Type: Article

References (35)

1. Tsukamoto, M.; Kagan, H. B. Adv. Synth. Catal. 2002, 344, 453
2. Reetz, M. T. Angew. Chem., Int. Ed. 2001, 40, 284
3. Reetz, M. T. Angew. Chem., Int. Ed. 2002, 41, 1335
4. Guo, J.; Wu, J.; Siuzdak, G.; Finn, M. G. Angew. Chem., Int. Ed. 1999, 38, 1755
5. Reetz, M. T.; Becker, M. H.; Klein, H.-W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758
6. Markert, C.; Pfaltz, A. Angew. Chem., Int. Ed. 2004, 43, 2498
7. Muller, C. A.; Markert, C.; Teichert, A. M.; Pfaltz, A. Chem. Commum. 2009, 1607
8. Reetz, M. T.; Becker, M. H.; Kuhling, K. M.; Holzwarth, A. Angew. Chem., Int. Ed. 1998, 37, 2647
9. Eelkema, R.; van Delden, R. A.; Feringa, B. L. Angew. Chem., Int. Ed. 2004, 43, 5013
10. Zhu, L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 3676
11. Zhu, L.; Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 4260
12. Folmer-Andersen, J. F.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 7986
13. Folmer-Andersen, J. F.; Kitamura, M.; Anslyn, E. V. J. Am. Chem. Soc. 2006, 128, 5652
14. Zhu, L.; Shabbir, S. H.; Anslyn, E. V. Chem. - Eur. J. 2007, 13, 99
15. Leung, D.; Folmer-Andersen, J. F.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12318
16. Leung, D.; Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12328
17. Shabbir, S. H.; Joyce, L. A.; da Cruz, G. M.; Lynch, V. M.; Sorey, S.; Anslyn, E. V. J. Am. Chem. Soc. 2009, 131, 13125
18. Shabbir, S. H.; Regan, C. J.; Anslyn, E. V. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 10487
19. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Nature 1995, 374, 345
20. Zhao, J.; Fyles, T. M.; James, T. D. Angew. Chem., Int. Ed. 2004, 43, 3461
21. Pu, L. Chem. Rev. 2004, 104, 1687
22. Li, Z.-B.; Lin, J.; Pu, L. Angew. Chem., Int. Ed. 2005, 44, 1690
23. Liu, H.-L.; Hou, X.-L.; Pu, L. Angew. Chem., Int. Ed. 2009, 48, 382
24. Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497
25. Nieto, S.; Lynch, V. M.; Anslyn, E. V.; Kim, H.; Chin, J. J. Am. Chem. Soc. 2008, 130, 9232
26. Parker, D. Chem. Rev. 1991, 91, 1441
27. Wenzel, T. J.; Wilcox, J. D. Chirality 2003, 15, 256
28. Wenzel, T. J. Discrimination of Chiral Compounds Using NMR; John Wiley & Sons: Hoboken, NJ, 2007.
29. Weisman, G. R. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1.
30. Fraser, R. R. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1.
31. Yang, D.; Li, X.; Fan, Y.-F.; Zhang, D.-W. J. Am. Chem. Soc. 2005, 127, 7996
32. Ma, F.-N.; Lin, J.; Lin, A.; Shen, X.-M.; Zhang, C. Org. Lett. 2006, 9, 125
33. Ema, T.; Tanida, D.; Sakai, T. J. Am. Chem. Soc. 2007, 129, 10591
34. Pirkle, W. H.; Hoover, D. J. Top. Stereochem. 1982, 1, 263
35. Jurs, P. C.; Bakken, G. A.; McClelland, H. E. Chem. Rev. 2000, 100, 2649