Chiral Carbon-rich Macrocycles and Cyclophanes

Carbon-Rich Compounds: From Molecules to Materials

Volumn , Issue , 2006, Pages 229-294

  Campbell, Katie ^a   Tykwinski, Rik R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Carbon rich compounds; Chiral carbon rich macrocycles and cyclophanes; Metal containing chiral macrocycles

Indexed keywords

EID: 84890997166     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527607994.ch6     Document Type: Chapter

References (121)

1. Solid-state structure depicted in ball and stick format using POV-Ray 3.6.0 (http://www.povray.org) and based on X-ray crystallog-raphic analysis and coordinates obtained from the Cambridge Crystallographic Data Centre (CCDC).
2. Synthesis of macrocycles and cyclophanes, see: C. S. Jones, M. J. O'Connor, M. M. Haley, in Acetylene Chemistry: Chemistry, Biology, and Material Science (F. Diederich, P. J. Stang, R. R. TYkwiNSki (eds.)), Wiley-VCH, Weinheim, 2005, Ch. 8;
3. Y. Tobe, M. Sonoda, in Modern Cyclophane Chemistry (R. Gleiter, H. Hopf (eds.)), Wiley-VCH, Weinheim, 2004, Ch. 1;
4. S. Hoger, Chem. Eur. J. 2004, 10, 1320-1329;
5. Y. Yamaguchi, Z. Yoshida, Chem. Eur. J. 2003, 9, 5430-5440;
6. D. Zhao, J. S. Moore, Chem. Commun. 2003, 807-818;
7. C. Grave, A. D. Schluter, Eur.J. Org. Chem. 2002, 3075-3098;
8. A. De Meijere, S. I. Kozhushkov, Top. Curr. Chem. 1999, 201, 1-42.
9. G. Simonneaux, P. Le Maux, Coord. Chem. Rev. 2002, 228, 43-60;
10. N. Kobayashi, Coord. Chem. Rev. 2001, 219, 99-123.
11. T. Fekner, J. Gallucci, M. K. Chan, J. Am. Chem. Soc. 2004, 126, 223-236, and references therein.
12. E. Engeldinger, D. Armspach, D. Matt, Chem. Rev. 2003, 103, 41474173.
13. T. W. Bell, N. M. Hext, Chem. Soc. Rev. 2004, 33, 589-598, and references therein.
14. H. A. Staab, E. Wehinger, W. Thorwart, Chem. Ber. 1972, 105, 2290-2309.
15. H. Irngartinger, Chem. Ber. 1973, 106, 761-772.
16. D. Solooki, J. D. Bradshaw, C. A. Tessier, W. J. Youngs, R. F. See, M. Churchill, J. D. Ferrara, J. Organomet. Chem. 1994, 470, 231-236.
17. R. Boese, A. J. Matzger, K. P. C. Vollhardt, J. Am. Chem. Soc. 1997, 119, 2052-2053.
18. M. M. Haley, M. L. Bell, S. C. Brand, D. B. Kimball, J. J. Pak, W. B. Wan, Tetrahedron Lett. 1997, 38, 74837486.
19. M. L. Bell, R. C. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. B. Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507-3520.
20. A. J. Boydston, L. Bondarenko, I. Dix, T. J. R. Weakley, H. Hopf, M. M. Haley, Angew. Chem. 2001, 113, 30743077; Angew. Chem. Int. Ed. 2001, 40, 2986-2989.
21. S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189-3192.
22. S. K. Collins, G. P. A. Yap, A. G. Fallis, Angew. Chem. 2000, 112, 393396; Angew. Chem. Int. Ed. 2000, 39, 385-388.
23. M. Ohkita, K. Ando, T. Suzuki, T. Tsuji, J. Org. Chem. 2000, 65, 43854390.
24. M. A. Heuft, S. K. Collins, A. G. Fallis, Org. Lett. 2003, 5, 1911-1914.
25. D. Zhang, C. A. Tessier, W. J. Youngs, Chem. Mater. 1999, 11, 30503057.
26. W. B. Wan, S. C. Brand, J. J. Pak, M. M. Haley, Chem. Eur. J. 2000, 6, 2044-2052.
27. T. Nishinaga, T. Kawamura, K. Komatsu, J. Org. Chem. 1997, 62, 5354-5362;
28. T. Nishinaga, T. Kawamura, K. Komatsu, Chem. Commun. 1998, 2263-2264.
29. R. M. Mcquilkin, P. J. Garratt, F. Sondheimer, J. Am. Chem. Soc. 1970, 92, 6682-6683.
30. X. Shen, D. M. Ho, R. A. Pascal Jr., Org. Lett. 2003, 5, 369-371.
31. K. Utsumi, T. Kawase, M. Oda, Chem. Lett. 2003, 32, 412-413.
32. B. Thulin, O. Wennerström, Acta Chem. Scand. B 1983, 37, 297-301.
33. B. Thulin, O. Wennerström, Tetrahedron Lett. 1977, 18, 929-930.
34. D. J. Cram, K. C. Dewhirst, J. Am Chem. Soc. 1959, 81, 5963-5971.
35. B. Thulin, O. Wennerström, I. Somfai, B. Chmieiarz, Acta Chem. Scand. B 1977, 31, 135-140;
36. I. Raston, O. Wennerström, Acta Chem. Scand. B 1982, 36, 655-660;
37. D. Tanner, B. Thulin, O. Wennerström, Acta Chem. Scand. B 1979, 33, 443-448.
38. M. A. Romero, A. G. Fallis, Tetrahedron Lett. 1994, 35, 4711-4714.
39. Y. Rubin, T. C. Parker, S. I. Khan, C. L. Holliman, S. W. Mcelvany, J. Am. Chem. Soc. 1996, 118, 53085309.
40. Y. Rubin, T. C. Parker, S. J. Pastor, S. Jalisatgi, C. Boulle, C. L. Wilkins, Angew. Chem. 1998, 110, 1353-1356; Angew. Chem. Int. Ed. 1998, 37, 1226-1229;
41. Y. Rubin, Chem. Eur. J. 1997, 3, 1009-1016.
42. Y. Tobe, N. Nakagawa, K. Naemura, T. Wakabayashi, T. Shida, Y. Achiba, J. Am. Chem. Soc. 1998, 120, 4544-4545;
43. Y. Tobe, H. Nakanishi, M. Sonoda, T. Wakabayashi, Y. Achiba, Chem. Commun. 1999, 1625-1626.
44. U. H. F. Bunz, Y. Rubin, Y. Tobe, Chem. Soc. Rev. 1999, 28, 107-119;
45. Y. Tobe, N. Nakagawa, J.-Y. Kishi, M. Sonoda, K. Naemura, T. Wakabayashi, T. Shida, Y. Achiba, Tetrahedron 2001, 57, 3629-3636.
46. Y. Tobe, R. Umeda, M. Sonoda, T. Wakabayashi, Chem. Eur. J. 2005, 11, 1603-1609.
47. H.-E. Högberg, O. Wennerström, Acta Chem. Scand. B, 1982, 36, 661667.
48. R. Herges, M. Deichmann, T. Wakita, Y. Okamoto, Angew. Chem. 2003, 115, 1202-1204; Angew. Chem. Int. Ed. 2003, 42, 1170-1172.
49. P. N. W. Baxter, J. Org. Chem. 2001, 66, 4170-4179.
50. A. S. Hay, J. Org. Chem. 1962, 27, 3320-3321.
51. P. N. W. Baxter, Chem. Eur. J. 2002, 8, 5250-5264.
52. M. A. Heuft, A. G. Fallis, Angew. Chem. 2002, 114, 4702-4705; Angew. Chem. Int. Ed. 2002, 41, 4520-4523.
53. P. N. W. Baxter, Chem. Eur. J. 2003, 9, 2531-2541.
54. T. Fekner, J. Gallucci, M. K. Chan, Org. Lett. 2004, 6, 989-992;
55. T. Fekner, J. Gallucci, M. K. Chan, J. Am. Chem. Soc. 2004, 126, 223-236.
56. N. Kobayashi, T. Fukuda, K. Ueno, H. Ogino, J. Am. Chem. Soc. 2001, 123, 10740-10741.
57. P. N. W. Baxter, J. Org. Chem. 2004, 69, 1813-1821.
58. A. Strand, B. Thulin, O. Wennerström, Acta Chem. Scand. B 1977, 31, 521-523.
59. M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885-887.
60. M. J. Marsella, R. J. Reid, Macro-molecules 1999, 32, 5982-5984.
61. T. Kauffmann, B. Greving, R. Kriegesmann, A. Mltschker, A. Woltermann, Chem. Ber. 1978, 111, 1330-1336;
62. T. Kauffmann, H. P. Mackowiak, Chem. Ber. 1985, 118, 2343-2352.
63. M. J. Marsella, Acc. Chem. Res. 2002, 35, 944-951.
64. M. J. Marsella, I. T. Kim, F. Tham, J. Am. Chem. Soc. 2000, 122, 974-975.
65. M. J. Marsella, G. Piao, F. S. Tham, Synthesis 2002, 1133-1135.
66. A. Rajca, A. Safronov, S. Rajca, R. Shoemaker, Angew. Chem. 1997, 109, 504-507; Angew. Chem., Int. Ed. Engl. 1997, 36, 488-491.
67. A. Rajca, A. Safronov, S. Rajca, J. Wongsriratanakul, J. Am. Chem. Soc. 2000, 122, 3351-3357.
68. S. Anderson, U. Neidlein, V. Grämlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1724; Angew. Chem, Int. Ed. Engl. 1995, 34, 15961600.
69. A. Bahr, A. S. Droz, M. Puntener, U. Neidlein, S. Anderson, P. Seiler, F. Diederich, Helv. Chim. Acta 1998, 81, 1931-1963.
70. A. S. Droz, F. Diederich, J. Chem. Soc., Perkin Trans. 1 2000, 4224-4226.
71. A. S. Droz, U. Neidlein, S. Anderson, P. Seiler, F. Diederich, Helv. Chim. Acta 2001, 84, 2243-2289.
72. K. Utsumi, T. Nakamura, T. Kawase, M. Oda, submitted.
73. D. L. An, T. Nakano, A. Orita, J. Otera, Angew. Chem. 2002, 114, 179181; Angew. Chem. Int. Ed. 2002, 41, 171-173.
74. L. Ma, L. Pu, Macromol. Chem. Phys. 1998, 199, 2395-2401.
75. H.-C. Zhang, W.-S. Huang, L. Pu, J. Org. Chem. 2001, 66, 481-487.
76. J. Lin, H.-C. Zhang, L. Pu, Org. Lett. 2002, 4, 3297-3300;
77. Z.-B. Li, J. Lin, H.-C. Zhang, M. Sabat, M. Hyacinth, L. Pu, J. Org. Chem. 2004, 69, 6284-6293;
78. J. Lin, Z.-B. Li, H.-C. Zhang, L. Pu, Tetrahedron Lett. 2004, 45, 103-106.
79. J. K. Judice, S. J. Keipert, D. J. Cram, J. Chem. Soc., Chem. Commun. 1993, 1323-1325.
80. For early examples of helicene based macrocycles, see: M. Joly, N. Defay, R. H. Martin, J. P. Declerq, G. Germain, B. Soubrier-Payen, M. Van Meerssche, Helv. Chim. Acta 1977, 60, 537-560;
81. P. J. Jessup, J. A. Reiss, Aust. J. Chem. 1976, 29, 173-178;
82. H. Numan, H. Wynberg, Tetrahedron Lett. 1975, 16, 1097-1100.
83. B. Thulin, O. Wennerström, Acta Chem. Scand. B 1976, 30, 688-690.
84. K. Nakamura, H. Okubo, M. Yamaguchi, Org. Lett. 2001, 3, 10971099.
85. Y. Saikl, K. Nakamura, Y. Nigorikawa, M. Yamaguchi, Angew. Chem. 2003, 115, 5348-5350; Angew. Chem. Int. Ed. 2003, 42, 5190-5192.
86. Y. Saikl, H. Sugiura, K. Nakamura, M. Yamaguchi, T. Hoshi, J.-I. Anzai, J. Am. Chem. Soc. 2003, 125, 92689269.
87. J. M. Fox, D. Lin, Y. Itagaki, T. Fujita, J. Org. Chem. 1998, 63, 20312038.
88. B. Kohler, V. Enkelmann, M. Oda, S. Pieraccini, G. P. Spada, U. Scherf, Chem. Eur. J. 2001, 7, 30003004.
89. S. Thorand, F. Vögtle, N. Krause, Angew. Chem. 1999, 111, 3929-3931; Angew. Chem. Int. Ed. 1999, 38, 37213723.
90. M. D. Clay, A. G. Fallis, Angew. Chem. 2005, 117, 4107-4110. Angew. Chem. Int. Ed 2005, 44, 4039-4042.
91. For a second, more recent example see: S. Odermatt, J. L. Alonso-Gömez, P. Seiler, M. M. Cid, F. Diederich, Angew. Chem. 2005, 117, 5203-5207; Angew. Chem. Int. Ed. 2005, 44, 5074-5078.
92. F. Gasparrini, D. Misiti, M. Pierini, C. Villani, Org. Lett. 2002, 4, 39933996.
93. Y. Tobe, T. Nagai, S. Araki, T. Ichikawa, A. Nomoto, M. Sonoda, K. Hirose, submitted.
94. B. Olenyuk, J. A. Whiteford, P. J. Stang, J. Am. Chem. Soc. 1996, 118, 8221-8230.
95. P. J. Stang, B. Olenyuk, D. C. Muddiman, R. D. Smith, Organo-metallics 1997, 16, 3094-3096.
96. C. Müller, J. A. Whiteford, P. J. Stang, J. Am. Chem. Soc. 1998, 120, 9827-9837.
97. A. Hori, A. Akasaka, K. Biradha, S. Sakamoto, K. Yamaguchi, M. Fujita, Angew. Chem. 2002, 114, 3403-3406; Angew. Chem. Int. Ed. 2002, 41, 3269-3272;
98. A. Hori, H. Kataoka, A. Akasaka, T. Okano, M. Fujita, J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3478-3485.
99. T. W. Kim, M. S. Lah, J.-I. Hong, Chem. Commun. 2001, 743-744.
100. A. Orita, T. Nakano, D. L. An, K. Tanikawa, K. Wakamatsu, J. Otera, J. Am. Chem. Soc. 2004, 126, 1038910396.
101. S. J. Lee, W. Lin, J. Am. Chem. Soc. 2002, 124, 4554-4555.
102. S. J. Lee, J. S. Kim, W. Lin, Inorg. Chem. 2004, 43, 6579-6588.
103. A. Lützen, M. Hapke, J. Griep-Raming, D. Haase, W. Saak, Angew. Chem. 2002, 114, 2190-2194; Angew. Chem. Int. Ed. 2002, 41, 2086-2089.
104. L. L. Schafer, T. D. Tilley, J. Am. Chem. Soc. 2001, 123, 2683-2684.
105. For selected examples see: R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111117;
106. W. J. Youngs, C. A. Tessier, J. D. Bradshaw, Chem. Rev. 1999, 99, 3153-3180;
107. E. Bosch, C. L. Barnes, Organometallics, 2000, 19, 5522-5524;
108. D. Xu, B. Hong, Angew. Chem. 2000, 112, 1896-1899; Angew. Chem. Int. Ed. 2000, 39, 18261829;
109. P. Siemsen, U. Gubler, C. Bosshard, P. Günter, F. Diederich, Chem. Eur. J. 2001, 7, 1333-1341;
110. H. Yao, M. Sabat, R. N. Grimes, F. Fabrizi De Biani, P. Zanello, Angew. Chem. 2003, 115, 1032-1035; Angew. Chem. Int. Ed. 2003, 42, 1002-1005;
111. K. Campbell, R. Mcdonald, M. J. Ferguson, R. R. Tykwinski, Organometallics 2003, 22, 1353-1355;
112. C. A. Johnson II, M. M. Haley, E. Rather, F. Han, T. J. R. Weakley, Organometallics 2005, 24, 1161-1172.
113. S. J. Lee, A. Hu, W. Lin, J. Am. Chem. Soc. 2002, 124, 12948-12949.
114. K. Sonogashira, T. Yatake, Y. Tohda, S. Takahashi, N. Hagihara, J. Chem. Soc., Chem. Commun. 1977, 291-292.
115. L. Zhang, Y.-H. Niu, A. K.-Y. Jen, W. Lin, Chem. Commun. 2005, 1002-1004.
116. H. Jiang, A. Hu, W. Lin, Chem. Commun. 2003, 96-97.
117. J. Hua, W. Lin, Org. Lett. 2004, 6, 861-864.
118. H. Jiang, W. Lin, J. Am. Chem. Soc. 2003, 125, 8084-8085.
119. H. Jiang, W. Lin, J. Am. Chem. Soc. 2004, 126, 7426-7427.
120. K. Campbell, C. A. Johnson II, R. Mcdonald, M. J. Ferguson, M. M. Haley, R. R. Tykwinski, Angew. Chem. 2004, 116, 6093-6097; Angew. Chem. Int. Ed. 2004, 43, 5967-5971.
121. K. Campbell, R. Mcdonald, M. J. Ferguson, R. R. Tykwinski, J. Organomet. Chem. 2003, 683, 379387.