Helix persistence and breakdown in oligoureas of metaphenylenediamine: Apparent diastereotopicity as a spectroscopic marker of helix length in solution

Journal of the American Chemical Society

Volumn 130, Issue 45, 2008, Pages 15193-15202

  Clayden, Jonathan ^a   Lemiègre, Loïc ^a,c   Morris, Gareth A ^a   Pickworth, Mark ^a   Snape, Timothy J ^a,d   Jones, Lyn H ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^d UNIVERSITY OF CENTRAL LANCASHIRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; BEARINGS (STRUCTURAL); METABOLISM; NUCLEAR MAGNETIC RESONANCE; OLIGOMERS; POLYMERS; STEREOCHEMISTRY; UREA;

AMIDE GROUPS; BENZYL GROUPS; EMPIRICAL METHODS; HELICITY; HELIX LENGTHS; NMR SIGNALS; SECONDARY STRUCTURES; STEREOGENIC CENTERS; SULFINYL GROUPS; SYNTHETIC PATHWAYS;

PORT TERMINALS;

AMIDE; BENZENE DERIVATIVE; OLIGOMER; PHENYLENEDIAMINE DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHIRALITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS;

CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PHENYLENEDIAMINES; POLYMERS; SOLUTIONS; STEREOISOMERISM; SULFINIC ACIDS;

EID: 57349142448     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805758v     Document Type: Article

References (83)

1. Eliel, E. L.; Wilen, S. H., Stereochemistry of Organic Compounds; Wiley: New York, 1994.
2. Hoffmann, R. W. Angew. Chem., Int. Ed. 2000, 39, 2054.
3. (a) Yamamoto, Y.; Nemoto, H.; Kikuchi, R.; Komatsu, H.; Suzuki, I. J. Am. Chem. Soc. 1990, 112, 8598.
4. (b) Alder, R. W; Anderson, K. R.; Benjes, P. A.; Butts, C. P.; Koutentis, P. A.; Orpen, A. G. Chem. Commun. 1998, 309.
5. (c) Stenkamp, D.; Hoffmann, R. W; Göttlich, R Eur. J. Org. Chem. 1999, 2929.
6. (d) Hoffmann, R. W.; Caturla, F.; Lazaro, M. A.; Framery, E.; Bernabeu, M. C.; Valancogne, I.; Montalbetti, C. A. G. N. New J. Chem. 2000, 24, 187.
7. (e) Carlier, P. R.; Zhang, Y.; Slebodnick, C.; Lo, M. M.-C.; Williams, I. D. J. Org. Chem. 2006, 71, 8835.
8. (f) O'Hagan, D.; Rzepa, H. S.; Schüler, M.; Slawin, A. M. Z. Beilstein J. Org. Chem. 2006, 2, 19.
9. (g) Hanessian, S.; Chahal, N.; Giroux, S. J. Org. Chem. 2006, 71, 7403.
10. Fukuzawa, A.; Tsuji, H.; Tamao, K. J. Am. Chem. Soc. 2006, 128, 6800.
11. Betson, M. S.; Clayden, J.; Helliwell, M.; Johnson, P.; Lai, L. W.; Pink, J. H.; Stimson, C. C.; Vassiliou, N.; Westlund, N.; Yasin, S. A.; Youssef, L. H. Org. Biomol. Chem. 2006, 4, 424.
12. Clayden, J. Chem. Commun. 2004, 127.
13. (a) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556.
14. (b) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033.
15. (c) Clayden, J.; Lai, L. W. Tetrahedron Lett. 2001, 42, 3163.
16. (d) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron 2004, 60, 4399.
17. (e) Betson, M. S.; Clayden, J.; Lam, H. K.; Helliwell, M. Angew. Chem., Int. Ed. 2005, 44, 1241.
18. (f) Clayden, J.; Westlund, N.; Frampton, C. S.; Helliwell, M. Org. Biomol. Chem. 2006, 4, 455.
19. (g) Clayden, J.; Vallverdú, L.; Helliwell, M. Org. Biomol. Chem. 2006, 4, 2106.
20. (a) Clayden, J.; Mitjans, D.; Youssef, L. H. J. Am. Chem. Soc. 2002, 124, 5266.
21. (b) Betson, M. S.; Clayden, J.; Helliwell, M.; Mitjans, D. Org. Biomol. Chem. 2005, 3, 3898.
22. (c) Clayden, J.; Worrall, C. P.; Moran, W.; Helliwell, M. Angew. Chem., Int. Ed. 2008, 47, 3234.
23. Betson, M. S.; Bracegirdle, A.; Clayden, J.; Helliwell, M.; Lund, A.; Pickworth, M.; Snape, T. J.; Worrall, C. P. Chem. Commun. 2007, 754.
24. Clayden, J.; Vassiliou, N. Org. Biomol. Chem. 2006, 4, 2667.
25. (a) Clayden, J.; Pink, J. H.; Yasin, S. A. Tetrahedron Lett. 1998, 39, 105.
26. (b) Clayden, J.; Kenworthy, M. N.; Youssef, L. H. Tetrahedron Lett. 2000, 41, 5171.
27. (c) Clayden, J.; Lai, L. W.; Helliwell, M. Tetrahedron: Asymmetry 2001, 12, 695.
28. (d) Clayden, J.; Lund, A.; Youssef, L. H. Org. Lett. 2001, 3, 4133.
29. (e) Clayden, J.; Vallverdú, L.; Helliwell, M. Chem. Commun. 2007, 2357.
30. Clayden, J.; Lund, A.; Vallverdú, L.; Helliwell, M. Nature (London) 2004, 431, 966.
31. (a) Hecht, S.; Huc, I. Foldamers; Wiley-VCH: Weinheim, 2007.
32. (b) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
33. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
34. Huc, I. Eur. J. Org. Chem. 2004, 17.
35. (a) Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013.
36. (b) Cornelissen, J. H. L. M.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. A. J. M. Chem. Rev. 2001, 101, 4039.
37. Dolain, C.; Grélard, A.; Laguerre, M.; Jiang, H.; Maurizot, V.; Huc, I. Chem. - Eur. J. 2005, 11, 6135.
38. (a) Akazome, M.; Ishii, Y.; Nireki, T.; Ogura, K. Tetrahedron Lett. 2008, 49, 4430.
39. (b) Maeda, K.; Yashima, E. Top. Curr. Chem. 2006, 265, 47.
40. (c) Yahima, E; Maeda, K.; Nishimura, T. Chem. - Eur. J. 2004, 10, 43.
41. (d) Jiang, H.; Dolain, C.; Léger, J.-M.; Gornitzka, H.; Huc, I. J. Am. Chem. Soc. 2004, 125, 1034.
42. (e) Mizutami, T.; Sakai, N.; Yagi, S.; Takagishi, T.; Kitagawa, S.; Ogoshi, H. J. Am. Chem. Soc. 2000, 122, 748.
43. (f) Pengo, B.; Formaggio, F.; Crisma, M.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J.; Saviano, M.; Iacovino, R.; Rossi, F.; Benedetti, E. J. Chem. Soc., Perkin Trans. 2 1998, 1651.
44. (g) Benedetti, E.; Saviano, M.; Iacovino, R.; Pedone, C.; Santini, A.; Crisma, M.; Formaggio, F.; Toniolo, C.; Broxterman, Q. R.; Kamphuis, J. Biopolymers 1998, 433.
45. Hu, H.-Y.; Xiang, J.-F.; Yang, Y.; Chen, C.-F. Org. Lett. 2008, 10, 1275.
46. Pijper, D.; Feringa, B. L. Angew. Chem., Int. Ed. 2007, 46, 3693.
47. Dolain, C.; Jiang, H.; Léger, J.-M.; Guionneau, P.; Huc, I. J. Am. Chem. Soc. 2005, 127, 12943.
48. (a) Miyagawa, T.; Furuko, A.; Maeda, K.; Katagiri, H.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2005, 127, 5018.
49. (b) 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.
50. (c) Inai, Y.; Komori, H. Biomacromolecules 2004, 5, 1231.
51. (d) Ousaka, N.; Inai, Y.; Okabe, T. Biopolymers 2006, 83, 337.
52. (e) Komori, H.; Inai, Y. J. Org. Chem. 2007, 72, 4012.
53. (a) Mikami, K.; Shimizu, M.; Zhang, H.-C.; Maryanoff, B. E. Tetrahedron 2001, 57, 2917.
54. (b) Mitchell, H. J.; Nelson, A.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1999, 1899.
55. (a) Noe, C. R.; Knollmüller, M.; Ettmayer, P. Angew. Chem., Int. Ed. 1988, 27, 1379.
56. (b) Jianfeng, Y.; RajanBabu, T. V.; Parquette, J. R. J. Am. Chem. Soc. 2008, 130, 7845.
57. Stone, M. T.; Heemstra, J. M.; Moore, J. S. Acc. Chem. Res. 2006, 39, 11.
58. Green, M. M.; Reola, C.; Muñoz, B.; Reidy, M. P. J. Am. Chem. Soc. 1988, 110, 4063.
59. Green, M. M.; Reidy, M. P.; Johnson, R. J.; Darling, G.; O'Leary, D. J.; Willson, G. J. Am. Chem. Soc. 1989, 111, 6452.
60. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
61. Maurizot, V.; Dolain, C.; Leydet, Y.; Léger, J.-M.; Guionneau, P.; Hue, I. J. Am. Chem. Soc. 2004, 126, 10049.
62. Jennings, W. B. Chem. Rev. 1975, 75, 307.
63. Schramm, M. P.; Rebek, J. New J. Chem. 2008, 32, 794.
64. (a) Lepore, G.; Migdal, S.; Blagdon, D. E.; Goodman, M. J. Org. Chem. 1973, 38, 2590.
65. (b) Lepore, U.; Castronuovo Lepore, G.; Ganis, P.; Germain, G.; Goodman, M. J. Org. Chem. 1976, 41, 2134.
66. (c) Yamaguchi, K.; Matsumura, G.; Kagechika, H.; Azumaya, L; Ito, Y.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1991, 113, 5474.
67. (d) Kurth, T. L.; Lewis, F. D. J. Am. Chem. Soc. 2003, 125, 13760.
68. Bhosale, S.; Sisson, A. L.; Sakai, N.; Matile, S. Org. Biomol. Chem. 2006, 3031.
69. Adler, T.; Bonjoch, J.; Clayden, J.; Font-Bardía, M.; Pickworth, M.; Solans, X.; Solé, D.; Vallverdú, L. Org. Biomol. Chem. 2005, 3173.
70. Clayden, J.; Lemiègre, L.; Pickworth, M.; Jones, L. Org. Biomol. Chem. 2008, 2908.
71. Clayden, J.; Lemiègre, L.; Helliwell, M. J. Org. Chem. 2007, 72, 2302.
72. Tanatani, A.; Kagechika, H.; Azumaya, I.; Fukutomi, R.; Ito, Y.; Yamaguchi, K.; Shudo, K. Tetrahedron Lett. 1997, 38, 4425.
73. Lewis, F. D.; Kurth, T. L.; Hattan, C. M.; Reiter, R. C.; Stevenson, C. D. Org. Lett. 2004, 6, 1605.
74. Clayden, J.; Stimson, C. C.; Keenan, M. Synlett 2005, 1716.
75. (a) García Ruano, J. L; Fernández-Ibáñez, M. A.; Maestro, M. C; Rodríguez-Fernández, M. M. J. Org. Chem. 2005, 70, 1796.
76. (b) Arroyo, Y.; Rodriguez, F.; Santos, M.; Sanz Tejedor, M. A.; García Ruano, J. L. J. Org. Chem. 2007, 72, 1035.
77. Andersen, K. K. Tetrahedron Lett. 1962, 93.
78. Clayden, J.; Dufour, J. Tetrahedron Lett. 2006, 47, 6945.
79. Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317.
80. Freeman, R.; Bax, A. J. Magn. Reson. 1980, 41, 507.
81. (a) Levitt, M. H. Concepts Magn. Res. 1995, 8, 77.
82. (b) Warren, W. S.; Richter, W.; Reotti, A. H.; Farmer, B. T. Science 1993, 262, 2005.
83. Ahmed, A.; Bragg, R. A.; Clayden, J.; Lai, L. W.; McCarthy, C.; Pink, J. H.; Westlund, N.; Yasin, S. A. Tetrahedron 1998, 54, 13277.