Stereocontrolled photodimerization with congested 1,8-Bis(4′-anilino) naphthalene templates

Journal of Organic Chemistry

Volumn 75, Issue 19, 2010, Pages 6653-6659

  Ghosn, Marwan W ^a   Wolf, Christia' ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; ACIDIC HYDROLYSIS; ACRYLIC ACIDS; AMIDE FORMATION; CINNAMOYL UNIT; CYCLOBUTANES; DICARBOXYLIC ACID; FUNCTIONAL GROUP TRANSFORMATIONS; HIGH YIELD; METHOXY; PARALLEL ARRANGEMENT; PHOTOCHEMICAL DIMERIZATION; PHOTODIMERIZATION; STEREO-SELECTIVE; SUZUKI CROSS COUPLING; UV IRRADIATION;

AMIDES; BUTANE; CARBOXYLIC ACIDS; CHLORINE COMPOUNDS; FUNCTIONAL GROUPS; ORGANIC ACIDS;

NAPHTHALENE;

1,8 BIS(3' METHYL 4' ANILINO)NAPHTHALENE; 1,8 BIS(4' ANILINO)NAPHTHALENE; 1,8 DIHALONAPHTHALENE; 3 (3,4 DIMETHYLPHENYL)ACRYLIC ACID; 3,4 BIS(3,4 DIMETHYLPHENYL)CYCLOBUTANE 1,2 DICARBOXYLIC ACID; 4 ACETAMIDOPHENYLBORONIC ACID; 4 METHOXY 3 METHYLPHENYLBORONIC ACID; ACRYLIC ACID DERIVATIVE; AMIDE; BETA TRUXINIC ACID; BORONIC ACID DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; HYDROCHLORIC ACID; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DIMERIZATION; STEREOCHEMISTRY; SUZUKI REACTION; ULTRAVIOLET RADIATION;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; DIMERIZATION; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES; PHOTOCHEMISTRY; STEREOISOMERISM;

EID: 77957155014     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101547w     Document Type: Article

References (80)

1. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025-1074
2. Khan, M.; Brunklaus, G.; Enkelmann, V.; Spiess, H.-W. J. Am. Chem. Soc. 2008, 130, 1741-1748
3. Fung, A. K. L.; Baker, W. R.; Fakhoury, S.; Stein, H. H.; Cohen, J.; Donner, B. G.; Garvey, D. S.; Spina, K. P.; Rosenberg, S. H. J. Med. Chem. 1997, 40, 2123-2125
4. Littman, L.; Tokar, C.; Venkatraman, S.; Roon, R. J.; Koerner, J. F.; Robinson, M. B.; Johnson, R. L. J. Med. Chem. 1999, 42, 1639-1647
5. Izquierdo, S.; Martin-Vila, M.; Moglioni, A. G.; Branchadell, V.; Ortuno, R. M. Tetrahedron: Asymmetry 2002, 13, 2403-2405
6. Martarello, L.; McConathy, J.; Camp, V. M.; Malveaux, E. J.; Simpson, N. E.; Simpson, C. P.; Olson, J. J.; Bowers, G. D.; Goodman, M. M. J. Med. Chem. 2002, 45, 2250-2259
7. Ichikawa, M.; Takahashi, M.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2004, 126, 16553-16558
8. Chi, Y.-M.; Nakamura, M.; Zhao, X.-Y.; Yoshizawa, T.; Yan, W.-M.; Hashimoto, F.; Kinjo, J.; Nohara, T.; Sakurada, S. Biol. Pharm. Bull. 2006, 29, 580-584
9. Russell, W. R.; Hanley, A. B.; Burkitt, M. J.; Chesson, A. Bioorg. Chem. 1999, 27, 339-350
10. Ito, Y.; Hosomi, H.; Ohba, S. Tetrahedron 2000, 56, 6833-6844
11. Koshima, H.; Ding, K.; Chisaka, Y.; Matsuura, T. J. Am. Chem. Soc. 1996, 118, 12059-12065
12. Koshima, H.; Nakagawa, T.; Matsuura, T. Tetrahedron Lett. 1997, 38, 6063-6066
13. Koshima, H.; Ding, K.; Chisaka, Y.; Matsuura, T.; Miyahara, I.; Hirotsu, K. J. Am. Chem. Soc. 1997, 119, 10317-10324
14. Ito, Y.; Hosomi, H.; Ohba, S. Tetrahedron 2000, 56, 6833-6844
15. MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. J. Am. Chem. Soc. 2000, 122, 7817-7818
16. Amirsakis, D. G.; Garcia-Garibay, M. A.; Rowan, S. J.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 2001, 40, 4256-4261
17. Friscic, T.; MacGillivray, L. R. Chem. Commun. 2003, 1306-1307
18. Ouyang, X.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2003, 125, 12400-12401
19. Gao, X.; Friscic, T.; MacGillivray, L. R. Angew. Chem., Int. Ed. 2004, 43, 232-236
20. Varshney, D. B.; Gao, X.; Friscic, T.; MacGillivray, L. R. Angew. Chem., Int. Ed. 2006, 45, 646-650
21. Yang, J.; Dewal, M. B.; Shimizu, L. S. J. Am. Chem. Soc. 2006, 128, 8122-8123
22. MacGillivray, L. R. J. Org. Chem. 2008, 73, 3311-3317
23. Yang, J.; Dewal, M. B.; Profeta, S., Jr.; Smith, M. D.; Li, Y.; Shimizu, L. S. J. Am. Chem. Soc. 2008, 130, 612-621
24. Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2000-2013
25. Schmidt, G. M. J. J. Chem. Soc. 1964, 2014-2021
26. Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641 - 3649 and references cited therein.
27. Caronna, T.; Liantonio, R.; Logothetis, T. A.; Metrangolo, P.; Pilati, T.; Resnati, G. J. Am. Chem. Soc. 2004, 126, 4500-4501
28. Goroff, N. S.; Curtis, S. M.; Webb, J. A.; Fowler, F. W.; Lauher, J. W. Org. Lett. 2005, 7, 1891-1893
29. Sokolov, A. N.; Friscic, T.; MacGillivray, L. R. J. Am. Chem. Soc. 2006, 128, 2806-2807
30. Nohra, B.; Graule, S.; Lescop, C.; Reau, R. J. Am. Chem. Soc. 2006, 128, 3520-3521
31. Berni, E.; Dolain, C.; Kauffmann, B.; Leger, J.-M.; Zhan, C.; Huc, I. J. Org. Chem. 2008, 73, 2687-2694
32. Peedikakkal, A. M. P.; Vittal, J. J. Chem.-Eur. J. 2008, 14, 5329-5334
33. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114-6127
34. Yamada, S.; Tokugawa, Y. J. Am. Chem. Soc. 2009, 131, 2098-2099
35. Tashiro, K.; Kamae, T.; Kobayashi, M.; Matsumoto, A.; Yokoi, K.; Aoki, S. Macromolecules 1999, 32, 2449-2454
36. Tanaka, T.; Matsumoto, A. J. Am. Chem. Soc. 2002, 124, 9676-9677
37. Matsumoto, A.; Tanaka, T.; Tsubouchi, T.; Tashiro, K.; Saragai, S.; Nakamato, S. J. Am. Chem. Soc. 2002, 124, 8891-8902
38. Matsumoto, A.; Oshita, S.; Fujioka, D. J. Am. Chem. Soc. 2002, 124, 13749-13756
39. Wu, D.-Y.; Chen, B.; Fu, X.-G.; Wu, L.-Z.; Zhang, L.-P.; Tung, C.-H. Org. Lett. 2003, 5, 1075-1077
40. Patrick, B. O.; Scheffer, J. R.; Scott, C. Angew. Chem., Int. Ed. 2004, 43, 3775-3777
41. Caronna, T.; Liantonio, R.; Logothetis, T. A.; Metrangolo, P.; Pilati, T.; Resnati, G. J. Am. Chem. Soc. 2004, 126, 4500-4501
42. Varshney, D. B.; Gao, X.; Friscic, T.; MacGillivray, L. R. Angew. Chem., Int. Ed. 2006, 45, 646-650
43. Wolf, C., Ed. Dynamic Stereochemistry of Chiral Compounds; RSC Publishing: Cambridge, UK, 2008; pp 302 - 304.
44. Ito, Y.; Borecka, B.; Trotter, J.; Scheffer, J. R. Tetrahedron Lett. 1995, 36, 6083-6086
45. Ito, Y.; Hosomi, H.; Ohba, S. Tetrahedron 2000, 56, 6833-6844
46. Ohba, S.; Hosomi, H.; Ito, Y. J. Am. Chem. Soc. 2001, 123, 6349-6352
47. Matsumoto, A.; Odani, T.; Chikada, M.; Sada, K.; Miyata, M. J. Am. Chem. Soc. 1999, 121, 11122-11129
48. Matsumoto, A.; Katayama, K.; Odani, T.; Oka, K.; Tashiro, K.; Saragai, S.; Nakamoto, S. Macromolecules 2000, 33, 7786-7792
49. Matsumoto, A.; Nagahama, S.; Odani, T. J. Am. Chem. Soc. 2000, 122, 9109-9119
50. Matsumoto, A.; Sada, K.; Tashiro, K.; Miyata, M.; Tsubouchi, T.; Tanaka, T.; Odani, T.; Nagahama, S.; Tanaka, T.; Inoue, K.; Saragai, S.; Nakamoto, S. Angew. Chem., Int. Ed. 2002, 41, 2502-2505
51. Nagahama, S.; Inoue, K.; Sada, K.; Miyata, M.; Matsumoto, A. Cryst. Growth Des. 2003, 3, 247-256
52. Mei, X.; Liu, S.; Wolf, C. Org. Lett. 2007, 9, 2729-2732
53. Hirano, S.; Toyota, S.; Toda, F.; Fujii, K.; Uekuasa, H. Angew. Chem., Int. Ed. 2006, 45, 6013-6016
54. Pattabiraman, M.; Natarajan, A.; Kaanumalle, L. S.; Ramamurthy, V. Org. Lett. 2005, 7, 529-532
55. Pattabiraman, M.; Kaanumalle, L. S.; Natarajan, A.; Ramamurthy, V. Langmuir 2006, 22, 7605-7609
56. Karthikeyan, S.; Ramamurthy, V. J. Org. Chem. 2007, 72, 452-458
57. Nishijima, M.; Wada, T.; Mori, T.; Pace, T. C. S.; Bohne, C.; Inoue, Y. J. Am. Chem. Soc. 2007, 129, 3478-3479
58. Takagi, K.; Suddaby, B. R.; Vadas, S. L.; Backer, C. A. J. Am. Chem. Soc. 1986, 108, 7865-7866
59. Nakamura, T.; Takagi, K.; Itoh, M.; Fujita, K.; Katsu, H.; Imae, T.; Sawaki, Y. J. Chem. Soc., Perkin Trans. 2 1997, 2751-2755
60. Amirsakis, D. G.; Elizarov, A. M.; Garcia-Garibay, M. A.; Glink, P. T.; Stoddart, F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 2003, 42, 1126-1132
61. Yamada, S.; Uematsu, N.; Tokugawa, Y. J. Am. Chem. Soc. 2007, 1'9, 12100-12101
62. Yuasa, H.; Nakatani, M.; Hashimoto, H. Org. Biomol. Chem. 2006, 4, 3694-3702
63. Selig, P.; Bach, T. J. Org. Chem. 2006, 71, 5662-5673
64. Fleming, S. A.; Parent, A. A.; Parent, E. E.; Pincock, J. A.; Renault, L. J. Org. Chem. 2007, 72, 9464-9470
65. Zitt, H.; Dix, I.; Hopf, H.; Jones, P. G. Eur. J. Org. Chem. 2002, 2298-2307
66. Wolf, C.; Ghebramariam, B. T. Tetrahedron: Asymmetry 2002, 13, 1153-1156
67. Wolf, C.; Tumambac, G. E. J. Phys. Chem. A 2003, 107, 815-817
68. Tumambac, G. E.; Wolf, C. J. Org. Chem. 2004, 69, 2048-2055
69. Tumambac, G. E.; Mei, X.; Wolf, C. Eur. J. Org. Chem. 2004, 3850-3856
70. Mei, X.; Wolf, C. Chem. Commun. 2004, 2078-2079
71. Mei, X.; Wolf, C. J. Am. Chem. Soc. 2004, 126, 14736-14737
72. Tumambac, G. E.; Wolf, C. J. Org. Chem. 2005, 70, 2930-2938
73. Tumambac, G. E.; Wolf, C. Org. Lett. 2005, 7, 4045-4048
74. Mei, X.; Martin, R. M.; Wolf, C. J. Org. Chem. 2006, 71, 2854-2861
75. Mei, X.; Wolf, C. Tetrahedron Lett. 2006, 47, 7901-7904
76. Wolf, C.; Liu, S.; Reinhardt, B. C. Chem. Commun. 2006, 4242-4244
77. Mei, X.; Wolf, C. J. Am. Chem. Soc. 2006, 128, 13326-13327
78. Liu, S.; Pestano, J. P. C.; Wolf, C. J. Org. Chem. 2008, 73, 4267-4270
79. Ghosn, M. W.; Wolf, C. J. Am. Chem. Soc. 2009, 131, 16360-16361
80. Kunio, S.; Hiroshi, T.; Eiko, N. Nihon Daigaku Seisankogakubu Kenkyu Hokuku, A: Rikokei 2003, 36, 49-60