Stereoselective UV sensing of 1,2-diaminocyclohexane isomers based on ligand displacement with a diacridylnaphthalene N,N′ -dioxide scandium complex

Journal of Organic Chemistry

Volumn 77, Issue 11, 2012, Pages 5203-5208

  Iwaniuk, Daniel P ^a   Yearick Spangler, Kimberly ^a   Wolf, Christian ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVE; LIGAND DISPLACEMENT; QUANTITATIVE DETECTION; STEREO-SELECTIVE; UV ABSORPTION; UV-SENSING;

ISOMERS; LIGANDS; SCANDIUM; STEREOCHEMISTRY; STEREOSELECTIVITY;

SCANDIUM COMPOUNDS;

1,2 DIAMINOCYCLOHEXANE; DIACRIDYLNAPHTHALENE N,N' DIOXIDE; NAPHTHALENE DERIVATIVE; SCANDIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; HIGH THROUGHPUT SCREENING; HYDROGEN BOND; STEREOCHEMISTRY; ULTRAVIOLET SPECTROSCOPY;

CATALYSIS; CYCLOHEXYLAMINES; ISOMERISM; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SCANDIUM; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84861835289     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300738s     Document Type: Article

References (50)

1. Gawley, R. E., Aubé, J., Ed. Principles of Asymmetric Synthesis. In Tetrahedron Organic Chemistry Series; Elsevier: New York, 1996.
2. Lin, G.-Q., Li, Y.-M., Chan, A. S. C., Ed. Principles and Applications of Asymmetric Synthesis; Wiley-VCH: New York, 2001.
3. Wolf, C., Ed. Dynamic Stereochemistry of Chiral Compounds; RSC Publishing: Cambridge, 2008; pp 180-398.
4. Eliel, E. L., Wilen, S. H., Ed. Stereochemistry of Organic Compounds; John Wiley and Sons: New York, 1994; pp 214-274.
5. Gao, X.; Kagan, H. B. Chirality 1998, 10, 120-124
6. Reetz, M. T.; Kuhling, K. M.; Hinrichs, H.; Deege, A. Chirality 2000, 12, 479-482
7. Welch, C. J.; Grau, B.; Moore, J.; Mathre, D. J. J. Org. Chem. 2001, 66, 6836-6837
8. Wolf, C.; Hawes, P. A. J. Org. Chem. 2002, 67, 2727-2729
9. Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733-1741
10. Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778
11. Ling, X.; Xiumin, S.; Cong, Z.; Koichi, M. Chirality 2005, 17, 476-480
12. Welch, C. J. Chirality 2009, 21, 114-118
13. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Nature 1995, 374, 345-347
14. Zhao, J.; Fyles, T. M.; James, T.; D. Angew. Chem., Int. Ed. 2004, 43, 3461-3464
15. Zhao, J.; Davidson, M. G.; Mahon, M. F.; Kociok-Koehn, G.; James, T. D. J. Am. Chem. Soc. 2004, 126, 16179-16186
16. Yang, W.; Yan, J.; Fang, H.; Wang, B. Chem. Commun. 2003, 792-793
17. Zhao, J.; James, T. D. J. Mater. Chem. 2005, 15, 2896-2901
18. Heinrichs, G.; Schellentraeger, M.; Kubik, S. Eur. J. Org. Chem. 2006, 4177-4186
19. Liang, X.; James, T. D.; Zhao, J. Tetrahedron 2008, 64, 1309-1315
20. Wu, Y.; Guo, H.; James, T. D.; Zhao, J. J. Org. Chem. 2011, 76, 5685-5695
21. Wu, Y.; Guo, H.; Zhang, X.; James, T. D.; Zhao, J. Chem.-Eur. J. 2011, 17, 7632-7644
22. Zhu, L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 3676-3677
23. Pagliari, S.; Corradini, R.; Galaverna, G.; Sforza, S.; Dossena, A.; Montalti, M.; Prodi, L.; Zaccheroni, N.; Marchelli, R. Chem.-Eur. J. 2004, 10, 2749-2758
24. Zhu, L.; Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 4260-4269
25. Folmer-Anderson, J. F.; Kitamura, M.; Anslyn, E. V. J. Am. Chem. Soc. 2006, 128, 5652-5653
26. Yang, X.; Liu, X.; Shen, K.; Zhu, C.; Cheng, Y. Org. Lett. 2011, 13, 3510-3513
27. Zhu, L.; Shabbir, S. H.; Anslyn, E. V. Chem.-Eur. J. 2007, 13, 99-104
28. Leung, D.; Folmer-Andersen, J. F.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12318-12327
29. Leung, D.; Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12328-12333
30. Lee, S. J.; Lin, W. J. Am. Chem. Soc. 2002, 124, 4554-4555
31. Lin, J.; Hu, Q.-S.; Xu, M.-H.; Pu, L. J. Am. Chem. Soc. 2002, 124, 2088-2089
32. Xu, M.-H.; Lin, J.; Hu, Q.-S.; Pu, L. J. Am. Chem. Soc. 2002, 124, 14239-14246
33. Li, Z.-B.; Lin, J.; Pu, L. Angew. Chem., Int. Ed. 2005, 44, 1690-1693
34. Liu, H.-L.; Zhu, H.-P.; Hou, X.-L.; Pu, L. Org. Lett. 2010, 12, 4172-4175
35. Yu, S.; Pu, L J. Am. Chem. Soc. 2010, 132, 17698-17700
36. Liu, H.-L.; Peng, Q.; Wu, Y.-D.; Chen, D.; Hou, X.-L.; Sabat, M.; Pu, L. Angew. Chem., Int. Ed. 2010, 49, 602-606
37. Jennings, K.; Diamond, D. Analyst 2001, 126, 1063-1067
38. Corradini, R.; Paganuzzi, C.; Marchelli, R.; Pagliari, S.; Sforza, S.; Dossema, A.; Galaverna, G.; Duchateau, A. J. Mater. Chem. 2005, 15, 2741-2746
39. Qing, G.-Y.; He, Y.-B.; Wang, F.; Qin, H.-J.; Hu, C.-G.; Yang, X. Eur. J. Org. Chem. 2007, 1768-1778
40. Tumambac, G. E.; Mei, X.; Wolf, C. Eur. J. Org. Chem. 2004, 3850-3856
41. Mei, X.; Wolf, C. Chem. Commun. 2004, 2078-2079
42. Mei, X.; Wolf, C. J. Am. Chem. Soc. 2004, 126, 14736-14737
43. Tumambac, G. E.; Wolf, C. Org. Lett. 2005, 7, 4045-4048
44. Mei, X.; Martin, R. M.; Wolf, C. J. Org. Chem. 2006, 71, 2854-2861
45. Mei, X.; Wolf, C. Tetrahedron Lett. 2006, 47, 7901-7904
46. Wolf, C.; Liu, S.; Reinhardt, B. C. Chem. Commun. 2006, 4242-4244
47. Mei, X.; Wolf, C. J. Am. Chem. Soc. 2006, 128, 13326-13327
48. Liu, S.; Pestano, J. P. C.; Wolf, C. J. Org. Chem. 2008, 73, 4267-4270
49. Satyanarayana, T; Abraham, S.; Kagan, H. B. Angew. Chem., Int. Ed. 2009, 48, 456-494
50. Trapp, O.; Schurig, V. Tetrahedron: Asymmetry 2010, 21, 1334-1340