Comprehensive chirality sensing: Development of stereodynamic probes with a Dual (chir)optical response

Journal of Organic Chemistry

Volumn 79, Issue 14, 2014, Pages 6517-6531

  Bentley, Keith W ^a   Wolf, Christian ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHIRALITY; CHROMOPHORES; CONDENSATION REACTIONS; FLUORESCENCE; FLUOROPHORES; HYDROGEN BONDS; NAPHTHALENE; PROBES; SCAFFOLDS;

ABSOLUTE CONFIGURATION; ASYMMETRIC TRANSFORMATIONS; CHIRAL AMPLIFICATION; INTRAMOLECULAR HYDROGEN BONDING; OPTICAL RESPONSE; SUBSTRATE BINDING; SUZUKI CROSS COUPLING REACTIONS; THREE-DIMENSIONAL STRUCTURE;

SUBSTRATES;

ANTHRACENE; NAPHTHALENE DERIVATIVE; SALICYLALDEHYDE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; CRYSTALLOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; KINETICS; POLYMERIZATION; RACEMIZATION; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 84904556128     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500959y     Document Type: Article

References (59)

1. Leung, D.; Kang, S. O.; Anslyn, E. V. Chem. Soc. Rev. 2012, 41, 448
2. Matile, S.; Berova, N.; Nakanishi, K.; Novkova, S.; Philpova, I.; Blagoev, B. J. Am. Chem. Soc. 1995, 117, 7021
3. Kurtan, T.; Nesnas, N.; Koehn, F. E.; Li, Y.-Q.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2001, 123, 5974
4. Huang, X.; Fujioka, N.; Pescitelli, G.; Koehn, F. E.; Williamson, R. T.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2002, 124, 10320
5. Balaz, M.; De Napoli, M.; Holmes, A. E.; Mammana, A.; Nakanishi, K.; Berova, N.; Purrello, R. Angew. Chem., Int. Ed. 2005, 44, 4006
6. Berova, N.; Pescitelli, G.; Petrovic, A. G.; Proni, G. Chem. Commun. 2009, 5958
7. Superchi, S.; Casarini, D.; Laurita, A.; Bavoso, A.; Rosini, C. Angew. Chem., Int. Ed. 2001, 40, 451
8. Superchi, S.; Bisaccia, R.; Casarini, D.; Laurita, A.; Rosini, C. J. Am. Chem. Soc. 2006, 128, 6893
9. Tartaglia, S.; Padula, D.; Scafato, P.; Chiummiento, L.; Rosini, C. J. Org. Chem. 2008, 73, 4865
10. Nieto, S.; Lynch, V.; Anslyn, E.; Kim, H.; Chin, J. J. Am. Chem. Soc. 2008, 130, 9232
11. Nieto, S.; Dragna, J.; Anslyn, E. Chem.-Eur. J. 2010, 16, 227
12. Leung, D.; Anslyn, E. Org. Lett. 2011, 13, 2298
13. Joyce, L. A.; Maynor, M. S.; Dragna, J. M.; da Cruz, G. M.; Lynch, V. M.; Canary, J. W.; Anslyn, E. V. J. Am. Chem. Soc. 2011, 133, 13746
14. Joyce, L.; Canary, J.; Anslyn, E. Chem.-Eur. J. 2012, 18, 8064
15. You, L.; Pescitelli, G.; Anslyn, E. V.; Di Bari, L. J. Am. Chem. Soc. 2012, 134, 7117
16. You, L.; Berman, J. S.; Lucksanawichien, A.; Anslyn, E. V. J. Am. Chem. Soc. 2012, 134, 7126
17. You, L.; Berman, J. S.; Anslyn, E. V. Nat. Chem. 2011, 3, 943
18. Holmes, A.; Zahn, S.; Canary, J. Chirality 2002, 14, 471
19. Holmes, A. E.; Das, D.; Canary, J. W. J. Am. Chem. Soc. 2007, 129, 1506
20. Canary, J. W.; Mortezaei, S.; Liang, J. Chem. Commun. 2010, 46, 5850
21. Yang, Q.; Olmsted, C.; Borhan, B. Org. Lett. 2002, 4, 3423
22. Li, X.; Tanasova, M.; Vasileiou, C.; Borhan, B. J. Am. Chem. Soc. 2008, 130, 1885
23. Li, X.; Borhan, B. J. Am. Chem. Soc. 2008, 130, 16126
24. Li, X.; Burrell, C. E.; Staples, R. J.; Borhan, B. J. Am. Chem. Soc. 2012, 134, 9026
25. Anyika, M.; Gholami, H.; Ashtekar, K. D.; Acho, R.; Borhan, B. J. Am. Chem. Soc. 2014, 136, 550
26. Mazaleyrat, J.-P.; Wright, K.; Gaucher, A.; Toulemonde, N.; Wakselman, M.; Oancea, S.; Peggion, C.; Formaggio, F.; Setnicka, V.; Keiderling, T. A.; Toniolo, C. J. Am. Chem. Soc. 2004, 126, 12874
27. Dutot, L.; Wright, K.; Gaucher, A.; Wakselman, M.; Mazaleyrat, J.-P.; De Zotti, M.; Peggion, C.; Formaggio, F.; Toniolo, C. J. Am. Chem. Soc. 2008, 130, 5986
28. Sciebura, J.; Skowronek, P.; Gawronski, J. Angew. Chem., Int. Ed. 2009, 48, 7069
29. Sciebura, J.; Gawronski, J. Chem.-Eur. J. 2011, 17, 13138
30. Ghosn, M. W.; Wolf, C. J. Am. Chem. Soc. 2009, 131, 16360
31. Ghosn, M. W.; Wolf, C. J. Org. Chem. 2011, 76, 3888
32. Ghosn, M. W.; Wolf, C. Tetrahedron 2011, 67, 6799
33. Iwaniuk, D. P.; Wolf, C. J. Am. Chem. Soc. 2011, 133, 2414
34. Iwaniuk, D. P.; Wolf, C. Org. Lett. 2011, 13, 2602
35. Iwaniuk, D. P.; Bentley, K. W.; Wolf, C. Chirality 2012, 24, 584
36. Iwaniuk, D. P.; Wolf, C. Chem. Commun. 2012, 48, 11226
37. Zhang, P.; Wolf, C. Chem. Commun. 2013, 49, 7010
38. Bentley, K. W.; Wolf, C. J. Am. Chem. Soc. 2013, 135, 12200
39. Bentley, K. W.; Wolf, C. J. Am. Chem. Soc. 2013, 135, 18052
40. Kim, H.; So, S. M.; Yen, C. P.-H.; Vinhato, E.; Lough, A. J.; Hong, J.-I.; Kim, H.-J.; Chin, J. Angew. Chem., Int. Ed. 2008, 47, 8657
41. Waki, M.; Abe, H.; Inouye, M. Angew. Chem., Int. Ed. 2007, 46, 3059
42. Katoono, R.; Kawai, H.; Fujiwara, K.; Suzuki, T. J. Am. Chem. Soc. 2009, 131, 16896
43. Wezenberg, S. J.; Salassa, G.; Escudero-Adan, E. C.; Benet-Buchholz, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2011, 50, 713
44. Kuwahara, S.; Nakamura, M.; Yamaguchi, A.; Ikeda, M.; Habata, Y. Org. Lett. 2013, 15, 5738
45. Kim, M. J.; Choi, Y. R.; Jeon, H.-G.; Kang, P.; Choi, M.-G.; Jeong, K.-S. Chem. Commun. 2013, 49, 11412
46. Wolf, C.; Bentley, K. W. Chem. Soc. Rev. 2013, 42, 5408
47. Song, F.; Wei, G.; Jiang, X.; Li, F.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 5772
48. Zou, W.; Yan, Y.; Fang, J.; Yang, Y.; Liang, J.; Deng, K.; Yao, J.; Wei, Z. J. Am. Chem. Soc. 2014, 136, 578
49. Bao, K.; Fan, A.; Dai, Y.; Zhang, L.; Zhang, W.; Cheng, M.; Yao, X. Org. Biomol. Chem. 2009, 7, 5084
50. Yadav, J.; Reddy, B.; Madan, C.; Hashim, R. Chem. Lett. 2000, 29, 738
51. Du, Z. T.; Lu, J.; Yu, H. R.; Xu, Y.; Li, A. P. J. Chem. Res. 2010, 34, 222
52. Bernard, A.; Ghiani, R.; Piras, P.; Rivoldini, A. Synthesis 1989, 287
53. In Dynamic Stereochemistry of Chiral Compounds; Wolf, C., Ed.; RSC Publishing: Cambridge, U.K., 2008; pp 84-94.
54. Cao, H.; Heagy, M. D. J. Fluoresc. 2004, 14, 569
55. Martínez-Máñez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419
56. Mei, X.; Wolf, C. Chem. Commun. 2004, 2078
57. Mei, X.; Wolf, C. J. Am. Chem. Soc. 2004, 126, 14736
58. Mei, X.; Wolf, C. J. Org. Chem. 2005, 70, 2299
59. Jones, G., II; Jackson, W. R.; Choi, C.-Y. J. Phys. Chem. 1985, 89, 294-300