Preparation of strained axially chiral (1,5)naphthalenophanes by photo-dehydro-diels-Alder reaction

Journal of the American Chemical Society

Volumn 133, Issue 8, 2011, Pages 2642-2650

  Wessig, Pablo ^a   Matthes, Annika ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; BOND ANGLE; CHIRAL HPLC; CIRCULAR DICHROISM SPECTRA; DIELS-ALDER; GEOMETRICAL PARAMETERS; HIGHLY STRAINED; HINDERED ROTATIONS; NAPHTHALENE MOIETIES; PHOTO-DEHYDRO-DIELS-ALDER REACTIONS; RING STRAINS; TRANSANNULAR INTERACTION;

CHIRALITY; DEFORMATION; DICHROISM; DIHEDRAL ANGLE; ENANTIOMERS;

NAPHTHALENE;

(1,5)NAPHTHALENOPHANE DERIVATIVE; HYDROGEN; NAPHTHALENE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL BOND; CHEMICAL REACTION; CIRCULAR DICHROISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PHOSPHORESCENCE; PHOTO DEHYDRO DIELS ALDER REACTION; SYNTHESIS;

CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; LUMINESCENT MEASUREMENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 79952267888     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109118m     Document Type: Article

References (69)

1. Halton, B. Advances in Strained and Interesting Organic Molecules. Vol. 8; JAI Press: Stamford, 2000.
2. Strained Hydrocarbons: Beyond the van't Hoff and Le Bel Hypothesis; Dodziuk, H., Ed.; Wiley-VCH: Weinheim, 2009.
3. Hopf, H. Classics in Hydrocarbon Chemistry: Synthesis, Concepts, Perspectives; Wiley-VCH: Weinheim, 2000.
4. Modern Cyclophane Chemistry; Gleiter, R., Hopf, H., Eds.; Wiley-VCH: Weinheim, 2004.
5. Bogdan, N. D.; Grosu, I. Curr. Org. Chem. 2009, 13, 502
6. Vögtle, F.; Schäfer, R.; Schunder, L.; Neumann, P. Liebigs Ann. Chem. 1970, 734, 102
7. Vögtle, F.; Neumann, P. Tetrahedron Lett. 1969, 60, 5329
8. Lüttringhaus, A.; Graalheer, H. Liebigs Ann. Chem. 1942, 550, 67
9. Lüttringhaus, A. Liebigs Ann. Chem. 1937, 528 (181) 203
10. Haenel, M. W. Tetrahedron Lett. 1978, 19, 4007
11. Haenel, M. W. Chem. Ber. 1978, 111, 1789
12. Blank, N. E.; Haenel, M. W. Chem. Ber. 1981, 114, 1520
13. Haenel, M. W. Chem. Ber. 1982, 115, 1425
14. Haenel, M. W.; Lintner, B.; Benn, R.; Rufinska, A.; Schroth, G.; Krueger, C.; Hirsch, S.; Irngartinger, H.; Schweitzer, D. Chem. Ber. 1985, 118, 4884
15. Lintner, B.; Schweitzer, D.; Benn, R.; Rufinska, A.; Haenel, M. W. Chem. Ber. 1985, 118, 4907
16. Haenel, M. W.; Lintner, B.; Benn, R.; Rufinska, A.; Schroth, G. Chem. Ber. 1985, 118, 4922
17. Corbellini, A.; Albenga, L. Gazz. Chim. Ital. 1931, 61, 111
18. Ando, T.; Nakagawa, M. Tetrahedron Lett. 1966, 7, 4437
19. Yoshida, M.; Tochiaki, Y.; Tatemitsu, H.; Sakata, Y.; Misumi, S. Chem. Lett. 1978, 829
20. Brown, H. S.; Muenchausen, C. P.; Sousa, L. R. J. Org. Chem. 1980, 45, 1682
21. Kovac, B.; Allan, M.; Heilbronner, E. Helv. Chim. Acta 1981, 64, 430
22. Chang, M. H.; Masek, B. B.; Dougherty, D. A. J. Am. Chem. Soc. 1985, 107, 1124
23. Nishimura, J.; Takeuchi, M.; Takahashi, H.; Ueda, E.; Matsuda, Y.; Oku, A. Bull. Chem. Soc. Jpn. 1989, 62, 3161
24. Asakawa, M.; Ashton, P. R.; Dehaen, W.; L'abbé, G.; Menzer, S.; Nouwen, J.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; Toppet, S.; White, A. J. P.; Williams, D. J. Chem.-Eur. J. 1997, 3, 772
25. Amabilino, D.; Ashton, P. R.; Balzani, V.; Boyd, S. E.; Credi, A.; Lee, J. Y.; Menzer, S.; Stoddart, J. F.; Venturi, M.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 4295
26. Rasadkina, E. N.; Nifant'ev, E. E. Russ. J. Gen. Chem. 1999, 69, 489
27. Ballardini, R.; Balzani, V.; Becher, J.; Fabio, A.; Gandolfi, M. T.; Mattersteig, G.; Nielsen, M. B.; Raymo, F. M.; Rowan, S. J.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 4120
28. Matsuda-Sentou, W.; Shinmyozu, T. Eur. J. Org. Chem. 2000, 18, 3195
29. Rasadkina, E. N.; Slitikov, P. V.; Mel'nik, M. S.; Nifant'ev, E. E. Russ. Chem. Bull. 2004, 53, 376
30. Mathews, M.; Tamaoki, N. J. Am. Chem. Soc. 2008, 130, 34
31. Suzuki, K.; Mori, K.; Ohmori, K. Angew. Chem., Int. Ed. 2009, 48, 5638
32. Wessig, P.; Müller, G.; Kühn, A.; Herre, R.; Blumenthal, H.; Troelenberg, S. Synthesis 2005, 1445
33. Wessig, P.; Müller, G. Chem. Commun. 2006, 4524
34. Wessig, P.; Müller, G.; Herre, R.; Kühn, A. Helv. Chim. Acta 2006, 89, 2694
35. Wessig, P.; Müller, G.; Pick, C.; Matthes, A. Synthesis 2007, 464
36. Wessig, P.; Müller, G. Chem. Rev. 2008, 108 (2008) 2051
37. Wessig, P.; Müller, G. Aust. J. Chem. 2008, 61, 569
38. Preparation of cyclophanes by Diels-Alder reaction: Cory, R. M.; McPhail, C. L.; Dikmans, A. J.; Vittal, J. Tetrahedron Lett. 1996, 37, 1983
39. Maynollo, J.; Kraeutler, B. Fullerene Sci. Tech. 1996, 4, 213
40. Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773
41. Brettreich, M.; Bendikov, M.; Chaffins, S.; Perepichka, D. F.; Dautel, O.; Duong, H.; Helgeson, R.; Wudl, F. Angew. Chem. Int. Ed. 2002, 41, 3688
42. Aly, A. A. Org. Biomol. Chem. 2003, 1, 756
43. Minuti, L.; Taticchi, A.; Lanari, D.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron: Asymm. 2003, 14, 2775
44. Franz, D.; Robbins, S. J.; Boere, R. T.; Dibble, P. W. J. Org. Chem. 2009, 74, 7544 Preparation of cyclophanes by Dehydro-Diels-Alder reaction
45. Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970
46. Rubin, M.; Sromek, A. W.; Gevorgian, V. Synlett 2003, 2265
47. Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901
48. Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232
49. Kawasaki, N.; Goto, M.; Kawabata, S.; Kometani, T. Tetrahedron Asymm. 2001, 12, 585
50. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1981, 22, 3815
51. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277
52. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651
53. Single-crystal X-ray diffraction analysis details of 10b were deposited with the Cambridge Crystallographic Database, CCDC No. 804691.
54. Crystal structure of 10g: Wessig, P.; Matthes, A.; Schilde, U. Z. Kristallogr. NCS 2010, 225, 744
55. Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384
56. Bringmann, G.; Gulder, T. A. M.; Reichert, M.; Gulder, T. Chirality 2008, 20, 628
57. Tobe, Y.; Takemura, A.; Jimbo, M.; Takahashi, T.; Kobiro, K.; Kakiuchi, K. J. Am. Chem. Soc. 1992, 114, 3479
58. McBride, J. M.; Keehn, P. M.; Wasserman, H. H. Tetrahedron Lett. 1969, 47, 4147
59. Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796
60. Dudev, T.; Lim, C. J. Am. Chem. Soc. 1998, 120, 4450
61. Wiberg, K. B. Angew. Chem., Int. Ed. 1986, 25, 312
62. Allinger, N. L.; Sprague, J. T.; Liljefors, T. J. Am. Chem. Soc. 1974, 96, 5100
63. Lindner, H. J. Tetrahedron. 1976, 32, 753
64. Jenneskens, L. W.; Louwen, J. N.; De Wolf, W. H.; Bickelhaupt, F. J. Phys. Org. Chem. 1990, 3, 295
65. Grimme, S. J. Am. Chem. Soc. 1992, 114, 10542
66. Tobe, Y.; Takemura, A.; Jimbo, M.; Takahashi, T.; Kobiro, K.; Kakiuchi, K. J. Am. Chem. Soc. 1992, 114, 3479
67. Tsuji, T.; Ohkita, M.; Konno, T.; Nishida, S. J. Am. Chem. Soc. 1997, 119, 8425
68. Stanger, A.; Ben-Mergui, N.; Perl, S. Eur. J. Org. Chem. 2003, 2709
69. Cope, A. C.; Martin, M. M.; McKervey, M. A. Q. Rev. Chem. Soc. 1966, 20, 119