Enantioselective fluorescence sensing of chiral α-amino alcohols

Journal of Organic Chemistry

Volumn 73, Issue 11, 2008, Pages 4267-4270

  Liu, Shuanglong ^a   Pestano, John Paul C ^a   Wolf, Christian ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; CHEMICAL REACTIONS; MICROFLUIDICS; POLYCYCLIC AROMATIC HYDROCARBONS;

AMINO ALCOHOLS; CHEMICAL EQUATIONS; CHLOROBENZOIC ACID; ENANTIOSELECTIVE;

NAPHTHALENE;

1,8 BIS(3 TERT BUTYL 9 ACRIDYL)NAPHTHALENE N,N' DIOXIDE; 2 CHLOROBENZOIC ACID; 3 TERT BUTYLANILINE; AMINOALCOHOL; ANILINE DERIVATIVE; CHLOROBENZOIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; FLUORESCENCE; REACTION ANALYSIS; SYNTHESIS;

EID: 44949156453     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800506a     Document Type: Article

References (35)

1. (a) Reetz, M. T.; Becker, M. H.; Kuhling, K. M.; Holzwarth, A. Angew. Chem., Int. Ed. 1998, 37, 2647-2650.
2. (b) Ding, K.; Shii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501.
3. (c) Guo, J.; Wu, J.; Siuzdak, G.; Finn, M. G. Angew. Chem., Int. Ed. 1999, 38, 1755-1758.
4. (d) Reetz, M. T.; Becker, M. H.; Klein, H.-W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758-1761.
5. (e) Reetz, M. T.; Kuhling; Deege, A.; Hinrichs, H.; Belder, D. Angew. Chem., Int. Ed. 2000, 39, 3891-3893.
6. (f) Abato, P.; Seto, C. T. J. Am. Chem. Soc. 2001, 123, 9206-9207.
7. (g) Evans, M. A.; Morken, J. P. J. Am. Chem. Soc. 2002, 124, 9020-9021.
8. (h) Taran, F.; Gauchet, C.; Mohar, B.; Meunier, S.; Valleix, A.; Renard, P. Y.; Creminon, C.; Grassi, J.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2002, 41, 124-127.
9. (i) Matsushita, M.; Yoshida, K.; Yamamoto, N.; Wirsching, P.; Lerner, R. A.; Janda, K. D. Angew. Chem., Int. Ed. 2003, 42, 5984-5987.
10. (j) Markert, C.; Pfaltz, A. Angew. Chem., Int. Ed. 2004, 43, 2498-2500.
11. (a) Pu, L. Chem. Rev. 2004, 104, 1687-1716.
12. (b) Pagliari, S.; Conadini, R.; Galaverna, G.; Sforza, S.; Dossena, A.; Montalti, M.; Prodi, L.; Zaccheroni, N.; Marchelli, R. Chem. Eur. J. 2004, 10, 2749-2758.
13. (c) Zhao, J.; Fyles, T. M.; James, T. D. Angew. Chem., Int. Ed. 2004, 43, 3461-3464.
14. (d) Zhu, L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 3676-3677.
15. (e) Li, Z.-B.; Lin, J.; Qin, Y.-C.; Pu, L. Org. Lett. 2005, 7, 3441-3444.
16. (f) Li, Z.-B.; Lin, J.; Pu, L. Angew. Chem., Int. Ed. 2005, 44, 1690-1693.
17. (g) Zhu, L.; Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 4260-4269.
18. (h) Folmer-Andersen, J. F.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 7986-7987.
19. (i) Mei, X.; Wolf, C. J. Am. Chem. Soc. 2006, 128, 13326-13327.
20. (a) Tumambac, G. E.; Mei, X.; Wolf, C. Eur. J. Org. Chem. 2004, 3850-3856.
21. (b) Mei, X.; Wolf, C. J. Am. Chem. Soc. 2004, 126, 14736-14737.
22. (c) Mei, X.; Wolf, C. Chem. Commun. 2004, 2078-2079.
23. (d) Tumambac, G. E.; Wolf, C. Org. Lett. 2005, 7, 4045-4048.
24. (e) Wolf, C.; Liu, S.; Reinhardt, B. C. Chem. Commun. 2006, 4242-4244.
25. (f) Mei, X.; Wolf, C. Tetrahedron Lett. 2006, 47, 7901-7904.
26. (a) Tumambac, G. E.; Wolf, C. J. Org. Chem. 2004, 69, 2048-2055.
27. (b) Tumambac, G. E.; Wolf, C. J. Org. Chem. 2005, 70, 2930-2938.
28. (c) Mei, X.; Wolf, C. J. Org. Chem. 2005, 70, 2299-2305.
29. (d) Mei, X.; Martin, R. M.; Wolf, C. J. Org. Chem. 2006, 71, 2854-2861.
30. (e) Wolf, C. Ed. Dynamic Stereochemistry of Chiral Compounds; RSC Publishing: London, UK, 2008; pp 84-109.
31. (a) Wolf, C.; Liu, S.; Mei, X.; August, A. T.; Casimir, M. D. J. Org. Chem. 2006, 71, 3270-3273.
32. (b) Mei, X.; August, A. T.; Wolf, C. J. Org. Chem. 2006, 71, 142-149.
33. (c) Liu, S.; Pestano, J. P. C.; Wolf, C. Synthesis 2007, 3519-3527.
34. 1,8-Diacridylnaphthalene 6 is formed in an anti/syn ratio of 55:45.
35. It should be noted that the use of racemic 1 can result in the formation of mixtures of homo- and heterochiral scandium complexes.