A racemic N,N′-dioxide-iron(III) complex chemosensor for determination of enantiomeric excess, concentration and identity of hydroxy carboxylic acids with circular dichroism and fluorescence responses

Tetrahedron Letters

Volumn 56, Issue 25, 2015, Pages 3882-3885

  Peng, Ruixue ^a   Lin, Lili ^a   Cao, Weidi ^a   Guo, Jing ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a,b  

^a Sichuan University   (China)

^b Chemical Engineering Research Center   (China)

Author keywords

Chemoselectivity; Chirality; Circular dichroism; Enantioselectivity; Hydroxy carboxylic acids; N,N Dioxide iron(III) complex

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; IRON COMPLEX; OXIDE;

ACCURACY; AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; CHEMOSENSOR; CHIRALITY; CIRCULAR DICHROISM; CONTROLLED STUDY; DERIVATIZATION; ENANTIOMER; ENANTIOSELECTIVITY; FLUORESCENCE; FLUORESCENCE ANALYSIS; MASS SPECTROMETRY; MEASUREMENT ACCURACY; QUANTITATIVE ANALYSIS; SENSOR; TITRIMETRY;

EID: 84930178214     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.04.101     Document Type: Article

References (57)

1. Principles of Asymmetric Synthesis R.E. Gawley, and J. Aubé Tetrahedron Organic Chemistry Series 1996 Elsevier New York
2. C. Wolf Dynamic Stereochemistry of Chiral Compounds 2008 RSC Cambridge 180 398
3. D. Leung, S.O. Kang, and E.V. Anslyn Chem. Soc. Rev. 41 2012 448 479
4. L. Zhu, and E.V. Anslyn J. Am. Chem. Soc. 126 2004 3676 3677
5. D. Leung, J.F. Folmer-Andersen, V.M. Lynch, and E.V. Anslyn J. Am. Chem. Soc. 130 2008 12318 12327
6. D. Leung, and E.V. Anslyn J. Am. Chem. Soc. 130 2008 12328 12333
7. S.H. Shabbir, L.A. Joyce, G.M. da Cruz, V.M. Lynch, S. Sorey, and E.V. Anslyn J. Am. Chem. Soc. 131 2009 13125 13131
8. D.P. Iwaniuk, K. Yearick-Spangler, and C.V. Wolf J. Org. Chem. 77 2012 5203 5208
9. R. Eelkema, R.A. van Delden, and B.L. Feringa Angew. Chem., Int. Ed. 43 2004 5013 5016
10. G.E. Tumambac, and C. Wolf Org. Lett. 7 2005 4045 4048
11. X. Mei, and C. Wolf J. Am. Chem. Soc. 126 2004 14736 14737
12. L. Zhu, Z. Zhong, and E.V. Anslyn J. Am. Chem. Soc. 127 2005 4260 4269
13. T.D. James, K.R.A.S. Sandanayake, and S. Shinkai Nature 374 1995 345 347
14. J.Z. Zhao, T.M. Fyles, and T.D. James Angew. Chem., Int. Ed. 43 2004 3461 3464
15. X. Mei, R.M. Martin, and C. Wolf J. Org. Chem. 71 2006 2854 2861
16. L. Pu Acc. Chem. Res. 45 2012 150 163
17. F.Y. Song, G. Wei, L. Wang, J.M. Jiao, Y.X. Cheng, and C.J. Zhu J. Org. Chem. 77 2012 4759 4764
18. L. You, G. Pescitelli, E.V. Anslyn, and L. Di Bari J. Am. Chem. Soc. 134 2012 7117 7125
19. C. Wolf, and K.W. Bentley Chem. Soc. Rev. 42 2013 5408 5424
20. M. Anyika, H. Gholami, K.D. Ashtekar, R. Acho, and B. Borhan J. Am. Chem. Soc. 136 2014 550 553
21. D. Leung, and E.V. Anslyn Org. Lett. 13 2011 2298 2301
22. L. You, J.S. Berman, and E.V. Anslyn Nat. Chem. 3 2011 943 948
23. H.H. Jo, C.Y. Lin, and E.V. Anslyn Acc. Chem. Res. 47 2014 2212 2221
24. P. Metola, E.V. Anslyn, T.D. James, and S.D. Bull Chem. Sci. 3 2012 156 161
25. K.W. Bentley, Y.G. Nam, J.M. Murphy, and C. Wolf J. Am. Chem. Soc. 135 2013 18052 18055
26. M.-S. Seo, A. Lee, and H. Kim Org. Lett. 16 2014 2950 2953
27. X. Huang, N. Fujioka, G. Pescitelli, F.E. Koehn, R.T. Williamson, K. Nakanishi, and N. Berova J. Am. Chem. Soc. 124 2002 10320 10335
28. J.-P. Mazaleyrat, K. Wright, A. Gaucher, N. Toulemonde, M. Wakselman, S. Oancea, C. Peggion, F. Formaggio, V. Setnicka, T.A. Keiderling, and C. Toniolo J. Am. Chem. Soc. 126 2004 12874 12879
29. S. Superchi, R. Bisaccia, D. Casarini, A. Laurita, and C. Rosini J. Am. Chem. Soc. 128 2006 6893 6902
30. A.E. Holmes, D. Das, and J.W. Canary J. Am. Chem. Soc. 129 2007 1506 1507
31. X. Li, M. Tanasova, C. Vasileiou, and B. Borhan J. Am. Chem. Soc. 130 2008 1885 1893
32. H. Kim, S.M. So, C.P.-H. Yen, E. Vinhato, A.J. Lough, J.-I. Hong, H.-J. Kim, and J. Chin Angew. Chem., Int. Ed. 47 2008 8657 8660
33. M.W. Ghosn, and C. Wolf J. Am. Chem. Soc. 131 2009 16360 16361
34. S.J. Wezenberg, G. Salassa, E.C. Escudero-Adan, J. Benet-Buchholz, and A.W. Kleij Angew. Chem., Int. Ed. 50 2011 713 716
35. V. Schurig J. Chromatogr., A 906 2001 275 299
36. M.S. Sigman, and E.N. Jacobsen J. Am. Chem. Soc. 120 1998 4901 4902
37. C.J. Welch, B. Grau, J. Moore, and D.J. Mathre J. Org. Chem. 66 2001 6836 6837
38. C. Wolf, and P.A. Hawes J. Org. Chem. 67 2002 2727 2729
39. X. Mei, and C. Wolf J. Am. Chem. Soc. 128 2006 13326 13327
40. C. Wolf, S. Liu, and B.C. Reinhardt Chem. Commun. 2006 4242 4244
41. L. Zhu, S.H. Shabbir, and E.V. Anslyn Chem. Eur. J. 13 2007 99 104
42. S. Liu, J.P.C. Pestano, and C. Wolf J. Org. Chem. 73 2008 4267 4270
43. S. Yu, and L. Pu J. Am. Chem. Soc. 132 2010 17698 17700
44. X. He, Q. Zhang, X.H. Liu, L.L. Lin, and X.M. Feng Chem. Commun. 2011 11641 11643
45. S. Yu, W. Plunkett, M. Kim, and L. Pu J. Am. Chem. Soc. 134 2012 20282 20285
46. S. Nieto, V. Lynch, E. Anslyn, H. Kim, and J. Chin J. Am. Chem. Soc. 130 2008 9232 9233
47. S. Nieto, V. Lynch, E. Anslyn, H. Kim, and J. Chin Org. Lett. 10 2008 5167 5170
48. S. Nieto, J.M. Dragna, and E.V. Anslyn Chem. Eur. J. 16 2010 227 232
49. K.W. Bentley, and C. Wolf J. Am. Chem. Soc. 135 2013 12200 12203
50. K.W. Bentley, and C. Wolf J. Org. Chem. 79 2014 6517 6531
51. P. Zhang, and C. Wolf Chem. Commun. 2013 7010 7012
52. X. Wu, X.-X. Chen, B.-N. Song, Y.-J. Huang, Z. Li, Z. Chen, T.D. James, and Y.-B. Jiang Chem. Eur. J. 20 2014 11793 11799
53. For reviews of chiral N,N′-dioxide-metal complexes in asymmetric catalysis, see: (a) X.H. Liu, L.L. Lin, and X.M. Feng Acc. Chem. Res. 44 2011 574
54. X.H. Liu, L.L. Lin, and X.M. Feng Org. Chem. Front. 1 2014 298
55. X. He, Q. Zhang, W.T. Wang, L.L. Lin, X.H. Liu, and X.M. Feng Org. Lett. 13 2011 804 807
56. Y.F. Cai, X.H. Liu, P.F. Zhou, Y.L. Kuang, L.L. Lin, and X.M. Feng Chem. Commun. 2013 8054 8056
57. P.C. Jurs, G.A. Baken, and H.E. McClelland Chem. Rev. 100 2000 2649 2678