2,2′-dihydroxybenzil: A stereodynamic probe for primary amines controlled by steric strain

Organic Letters

Volumn 16, Issue 11, 2014, Pages 2950-2953

  Seo, Min Seob ^a,b   Lee, Ansoo ^a,b   Kim, Hyunwoo ^a,b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Institute for Basic Science   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2,2'-DIHYDROXYBENZIL; AMINE; DRUG DERIVATIVE; NAPHTHALENE DERIVATIVE; PHENYLGLYOXAL; SALICIL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; QUANTUM THEORY; STEREOISOMERISM;

AMINES; CIRCULAR DICHROISM; MOLECULAR STRUCTURE; NAPHTHALENES; PHENYLGLYOXAL; QUANTUM THEORY; STEREOISOMERISM;

EID: 84902083809     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501088v     Document Type: Article

References (58)

1. Miyake, H.; Tsukube, H. Chem. Soc. Rev. 2012, 41, 6977
2. Crassous, J. Chem. Commun. 2012, 48, 9684
3. Gong, L.; Wenzel, M.; Meggers, E. Acc. Chem. Res. 2013, 46, 2635
4. Meggers, E. Eur. J. Inorg. Chem. 2011, 2911
5. Meggers, E. Chem. Commun. 2009, 1001
6. Crassous, J. Chem. Soc. Rev. 2009, 38, 830
7. Wolf, C.; Bentley, K. W. Chem. Soc. Rev. 2013, 42, 5408
8. Leung, D.; Kang, S. O.; Anslyn, E. V. Chem. Soc. Rev. 2012, 41, 448
9. Berova, N.; Bari, L. D.; Pescitelli, G. Chem. Soc. Rev. 2007, 36, 914
10. Bentley, K. W.; Wolf, C. J. Am. Chem. Soc. 2013, 135, 12200
11. Zhang, P.; Wolf, C. Chem. Commun. 2013, 49, 7010
12. Joyce, L. A.; Canary, J. W.; Anslyn, E. V. Chem.-Eur. J. 2012, 18, 8064
13. Iwaniuk, D. P.; Bentley, K. W.; Wolf, C. Chirality 2012, 24, 584
14. Ghosn, M. W.; Wolf, C. J. Org. Chem. 2011, 76, 3888
15. Ściebura, J.; Gawroński, J. Chem.-Eur. J. 2011, 17, 13138
16. Ghosn, M. W.; Wolf, C. Tetrahedron 2011, 67, 6799
17. Nieto, S.; Dragna, J. M.; Anslyn, E. V. Chem.-Eur. J. 2010, 16, 227
18. Ghosn, M. W.; Wolf, C. J. Am. Chem. Soc. 2009, 131, 16360
19. 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
20. Nieto, S.; Lynch, V. M.; Anslyn, E. V.; Kim, H.; Chin, J. J. Am. Chem. Soc. 2008, 130, 9232
21. Holmes, A. E.; Das, D.; Canary, J. W. J. Am. Chem. Soc. 2007, 129, 1506
22. Li, X.; Burrell, C. E.; Staples, R. J.; Borhan, B. J. Am. Chem. Soc. 2012, 134, 9026
23. Li, X.; Borhan, B. J. Am. Chem. Soc. 2008, 130, 16126
24. Li, X.; Tanasova, M.; Vasileiou, C.; Borhan, B. J. Am. Chem. Soc. 2008, 130, 1885
25. Tartaglia, S.; Padula, D.; Scafato, P.; Chiummiento, L.; Rosini, C. J. Org. Chem. 2008, 73, 4865
26. Dutot, L.; Wright, K.; Gaucher, A.; Wakselman, M.; Mazaleyrat, J.-P.; Zotti, M. D.; Peggion, C.; Formaggio, F.; Toniolo, C. J. Am. Chem. Soc. 2008, 130, 5986
27. Waki, M.; Abe, H.; Inouye, M. Angew. Chem., Int. Ed. 2007, 46, 3059
28. Gawroński, J.; Kwit, M.; Gawrońska, K. Org. Lett. 2002, 4, 4185
29. Superchi, S.; Casarini, D.; Laurita, A.; Bavoso, A.; Rosini, C. Angew. Chem., Int. Ed. 2001, 40, 451
30. Hosoi, S.; Kamiya, M.; Ohta, T. Org. Lett. 2001, 3, 3659
31. Wezenberg, S. J.; Salassa, G.; Escudero-Adán, E. C.; Benet-Buchholz, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2011, 50, 713
32. 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
33. Superchi, S.; Bisaccia, R.; Casarini, D.; Laurita, A.; Rosini, C. J. Am. Chem. Soc. 2006, 128, 6893
34. Mei, X.; Wolf, C. J. Am. Chem. Soc. 2004, 126, 14736
35. Proni, G.; Pescitelli, G.; Huang, X.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2003, 125, 12914
36. Iwaniuk, D. P.; Wolf, C. Chem. Commun. 2012, 48, 11226
37. Leung, D.; Anslyn, E. V. Org. Lett. 2011, 13, 2298
38. Katoono, R.; Kawai, H.; Fujiwara, K.; Suzuki, T. J. Am. Chem. Soc. 2009, 131, 16896
39. Ściebura, J.; Skowronek, P.; Gawronski, J. Angew. Chem., Int. Ed. 2009, 48, 7069
40. Mazaleyrat, J.-P.; Wright, K.; Gaucher, A.; Toulemonde, N.; Wakselman, M.; Oancea, S.; Peggion, C.; Formaggio, F.; Setnička, V.; Keiderling, T. A.; Toniolo, C. J. Am. Chem. Soc. 2004, 126, 12874
41. Iwaniuk, D. P.; Wolf, C. J. Am. Chem. Soc. 2011, 133, 2414
42. Iwaniuk, D. P.; Wolf, C. Org. Lett. 2011, 13, 2602
43. Borovkov, V. V.; Hembury, G. A.; Inoue, Y. Acc. Chem. Res. 2004, 37, 449
44. Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. J. Am. Chem. Soc. 2001, 123, 2979
45. Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. Org. Lett. 2000, 2, 1565
46. Kuwahara, S.; Nakamura, M.; Yamaguchi, A.; Ikeda, M.; Habata, Y. Org. Lett. 2013, 15, 5738
47. Bentley, K. W.; Nam, Y. G.; Murphy, J. M.; Wolf, C. J. Am. Chem. Soc. 2013, 135, 18052
48. Escárcega-Bobadilla, M. V.; Salassa, G.; Belmonte, M. M.; Escudero-Adán, E. C.; Kleij, A. W. Chem.-Eur. J. 2012, 18, 6805
49. You, L.; Pescitelli, G.; Anslyn, E. V.; Bari, L. D. J. Am. Chem. Soc. 2012, 134, 7117
50. You, L.; Berman, J. S.; Lucksanawichien, A.; Anslyn, E. V. J. Am. Chem. Soc. 2012, 134, 7126
51. You, L.; Berman, J. S.; Anslyn, E. V. Nat. Chem. 2011, 3, 943
52. Dragna, J. M.; Pescitelli, G.; Tran, L.; Lynch, V. M.; Anslyn, E. V.; Bari, L. D. J. Am. Chem. Soc. 2012, 134, 4398
53. So, S. M.; Moozeh, K.; Lough, A. J.; Chin, J. Angew. Chem., Int. Ed. 2014, 53, 829
54. Kim, H.; Nguyen, Y.; Yen, C. P.-H.; Chagal, L.; Lough, A. J.; Kim, B. M.; Chin, J. J. Am. Chem. Soc. 2008, 130, 12184
55. Kim, H.; Nguyen, Y.; Lough, A. J.; Chin, J. Angew. Chem., Int. Ed. 2008, 47, 8678
56. Park, H.; Kim, K. M.; Lee, A.; Ham, S.; Nam, W.; Chin, J. J. Am. Chem. Soc. 2007, 129, 1518
57. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2000, 122, 10405
58. Ziegler, M.; Zelewsky, A. v. Coord. Chem. Rev. 1998, 177, 257