Enantioselective synthesis of planar-chiral carba-paracyclophanes: Rhodium-catalyzed [2+2+2] cycloaddition of cyclic diynes with terminal monoynes

Angewandte Chemie - International Edition

Volumn 52, Issue 21, 2013, Pages 5617-5621

  Araki, Tatsuya ^a   Noguchi, Keiichi ^a   Tanaka, Ken ^a,b  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

alkynes; asymmetric catalysis; cycloadditions; cyclophanes; rhodium

Indexed keywords

[2+2+2] CYCLOADDITION; ALKYNES; ASYMMETRIC CATALYSIS; CYCLOADDITIONS; CYCLOPHANES; ENANTIOSELECTIVE SYNTHESIS; HIGH SUBSTRATE CONCENTRATIONS; RHODIUM-CATALYZED;

CATALYSIS; CYCLOADDITION; ENANTIOSELECTIVITY;

RHODIUM;

EID: 84877722090     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300696     Document Type: Article

References (100)

1. F. Vögtle, Cyclophane Chemistry, Wiley, Chichester, 1993
2. Modern Cyclophane Chemistry, (Eds.:, R. Gleiter, H. Hopf,), Wiley-VCH, Weinheim, 2004.
3. For a review of the cyclophane synthesis, see:, V. V. Kane, W. H. DeWolf, F. Bickelhaupt, Tetrahedron 1994, 50, 4575.
4. For a review of the transition-metal-catalyzed synthesis of compounds with non-centrochirality, see:, M. Ogasawara, S. Watanabe, Synthesis 2009, 1761.
5. K. Tanaka, T. Hori, T. Osaka, K. Noguchi, M. Hirano, Org. Lett. 2007, 9, 4881
6. T. Hori, Y. Shibata, K. Tanaka, Tetrahedron: Asymmetry 2010, 21, 1303.
7. K. Kanda, T. Koike, K. Endo, T. Shibata, Chem. Commun. 2009, 1870.
8. K. Kanda, K. Endo, T. Shibata, Org. Lett. 2010, 12, 1980
9. K. Kanda, R. Hamanaka, K. Endo, T. Shibata, Tetrahedron 2012, 68, 1407.
10. N. Kanomata, Y. Ochiai, Tetrahedron Lett. 2001, 42, 1045
11. N. Kanomata, J. Oikawa, Tetrahedron Lett. 2003, 44, 3625
12. T. Ueda, N. Kanomata, H. Machida, Org. Lett. 2005, 7, 2365
13. N. Kanomata, G. Mishima, J. Onozato, Tetrahedron Lett. 2009, 50, 409.
14. K. Mori, K. Ohmori, K. Suzuki, Angew. Chem. 2009, 121, 5748
15. Angew. Chem. Int. Ed. 2009, 48, 5638.
16. D. J. Cram, H. U. Daeniker, J. Am. Chem. Soc. 1954, 76, 2743
17. D. J. Cram, M. F. Antar, J. Am. Chem. Soc. 1958, 80, 3109
18. V. V. Kane, A. D. Wolf, M. Jones, Jr., J. Am. Chem. Soc. 1974, 96, 2643
19. P. G. Gassman, T. F. Bailey, R. C. Hoye, J. Org. Chem. 1980, 45, 2923
20. Y. Tobe, K. Kakiuchi, Y. Odaira, T. Hosaki, Y. Kai, N. Kasai, J. Am. Chem. Soc. 1983, 105, 1376
21. J. Liebe, W. Tochtermann, J. Weiss, Tetrahedron Lett. 1983, 24, 2549
22. J. Liebe, C. Wolff, C. Krieger, J. Weiss, W. Tochtermann, Chem. Ber. 1985, 118, 4144
23. L. W. Jenneskens, F. J. J. DeKanter, P. A. Kraakman, L. A. M. Turkenburg, W. E. Koolhaas, W. H. DeWolf, F. Bickelhaupt, Y. Tobe, K. Kakiuchi, Y. Odaira, J. Am. Chem. Soc. 1985, 107, 3716
24. G. B. M. Kostermans, W. H. DeWolf, F. Bickelhaupt, Tetrahedron Lett. 1986, 27, 1095
25. H. Higuchi, K. Tani, T. Otsubo, Y. Sakata, S. Misumi, Bull. Chem. Soc. Jpn. 1987, 60, 4027
26. U. Vagt, M. Haase, J. Konusch, W. Tochtermann, Chem. Ber. 1987, 120, 769
27. Y. Tobe, A. Nakayama, K. Kakiuchi, Y. Odaira, Y. Kai, N. Kasai, J. Org. Chem. 1987, 52, 2639
28. M. Takeshita, M. Tashiro, A. Tsuge, Chem. Ber. 1991, 124, 1403
29. M. Takeshita, H. Tsuzuki, M. Tashiro, Bull. Chem. Soc. Jpn. 1992, 65, 2076
30. D. V. Hochmuth, W. A. König, Tetrahedron: Asymmetry 1999, 10, 1089
31. J. Tae, Y.-K. Yang, Org. Lett. 2003, 5, 741
32. T. Tsuji, M. Okuyama, M. Ohkita, H. Kawai, T. Suzuki, J. Am. Chem. Soc. 2003, 125, 951
33. V. E. Ziffle, P. Cheng, D. L. J. Clive, J. Org. Chem. 2010, 75, 8024.
34. K. Tanaka, K. Shirasaka, Org. Lett. 2003, 5, 4697
35. K. Tanaka, K. Toyoda, A. Wada, K. Shirasaka, M. Hirano, Chem. Eur. J. 2005, 11, 1145
36. K. Tanaka, H. Sagae, K. Toyoda, K. Noguchi, Eur. J. Org. Chem. 2006, 3575.
37. Y. Shibata, K. Tanaka, Synthesis 2012, 323
38. K. Tanaka, Heterocycles 2012, 85, 1017
39. K. Tanaka, Synlett 2007, 1977
40. M. Fujiwara, I. Ojima, in Modern Rhodium-Catalyzed Organic Reactions (Ed.:, P.A. Evans,), Wiley-VCH, Weinheim, 2005, chap. 7, p. 129.
41. A. F. Moretto, H.-C. Zhang, B. E. Maryanoff, J. Am. Chem. Soc. 2001, 123, 3157
42. L. V. R. Boñaga, H.-C. Zhang, D. A. Gauthier, I. Reddy, B. E. Maryanoff, Org. Lett. 2003, 5, 4537
43. L. V. R. Boñaga, H.-C. Zhang, B. E. Maryanoff, Chem. Commun. 2004, 2394
44. 3-catalyzed [2+2+2] cycloaddition, see
45. H. Kinoshita, H. Shinokubo, K. Oshima, J. Am. Chem. Soc. 2003, 125, 7784.
46. S. Saito, N. Tsuboya, Y. Yamamoto, J. Org. Chem. 1997, 62, 5042
47. D. Weibel, V. Gevorgyan, Y. Yamamoto, J. Org. Chem. 1998, 63, 1217
48. V. Gevorgyan, N. Tsuboya, Y. Yamamoto, J. Org. Chem. 2001, 66, 2743. Cycloaddition of Fischer chromium carbenes with alkynes
49. K. H. Dötz, A. Gerhardt, J. Organomet. Chem. 1999, 578, 223
50. H. Wang, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 2000, 122, 9862
51. H. Wang, J. Huang, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 2003, 125, 8980; Intramolecular addition of rhodium carbenes
52. M. P. Doyle, W. Hu, B. Chapman, A. B. Marnett, C. S. Peterson, J. P. Vitale, S. A. Stanley, J. Am. Chem. Soc. 2000, 122, 5718
53. M. P. Doyle, W. Hu, Synlett 2001, 1364; Palladium-catalyzed Heck reaction
54. X. Geng, M. L. Miller, S. Lin, I. Ojima, Org. Lett. 2003, 5, 3733
55. G. Dyker, D. Kadzimirsz, G. Henkel, Tetrahedron Lett. 2003, 44, 7905.
56. T. Araki, D. Hojo, K. Noguchi, K. Tanaka, Synlett 2011, 539.
57. K. Tanaka, H. Sagae, K. Toyoda, K. Noguchi, M. Hirano, J. Am. Chem. Soc. 2007, 129, 1522
58. K. Tanaka, H. Sagae, K. Toyoda, M. Hirano, Tetrahedron 2008, 64, 831.
59. T. Shibata, T. Uchiyama, K. Endo, Org. Lett. 2009, 11, 3906
60. T. Shibata, M. Miyoshi, T. Uchiyama, K. Endo, N. Miura, K. Monde, Tetrahedron 2012, 68, 2679.
61. R. Gleiter, Angew. Chem. 1992, 104, 29
62. Angew. Chem. Int. Ed. Engl. 1992, 31, 27
63. R. Gleiter, M. Merger, Angew. Chem. 1997, 109, 2532
64. Angew. Chem. Int. Ed. Engl. 1997, 36, 2426; For recent examples, see
65. G. Haberhauer, F. Rominger, R. Gleiter, Angew. Chem. 1998, 110, 3632
66. Angew. Chem. Int. Ed. 1998, 37, 3376
67. V. Wolfart, M. Ramming, R. Gleiter, B. Nuber, H. Pritzkow, F. Rominger, Eur. J. Inorg. Chem. 1999, 499
68. R. J. Schaller, G. Haberhauer, R. Gleiter, F. Rominger, Eur. J. Inorg. Chem. 2002, 2296
69. D. B. Werz, J. H. Schulte, R. Gleiter, F. Rominger, J. Organomet. Chem. 2004, 689, 3132.
70. A. Pla-Quintana, A. Roglans, A. Torrent, M. Moreno-Mañas, J. Benet-Buchholz, Organometallics 2004, 23, 2762
71. A. Torrent, I. González, A. Pla-Quintana, A. Roglans, M. Moreno-Mañas, T. Parella, J. Benet-Buchholz, J. Org. Chem. 2005, 70, 2033
72. I. González, S. Bouquillon, A. Roglans, J. Muzart, Tetrahedron Lett. 2007, 48, 6425
73. I. González, A. Pla-Quintana, A. Roglans, Synlett 2009, 2844
74. S. Brun, M. Parera, A. Pla-Quintana, A. Roglans, T. Leõn, T. Achard, J. Solà, X. Verdaguer, A. Riera, Tetrahedron 2010, 66, 9032
75. S. Brun, A. Torrent, A. Pla-Quintana, A. Roglans, X. Fontrodona, J. Benet-Buchholz, T. Parella, Organometallics 2012, 31, 318.
76. M. Ogasawara, W.-Y. Wu, S. Arae, S. Watanabe, T. Morita, T. Takahashi, K. Kamikawa, Angew. Chem. 2012, 124, 3005
77. Angew. Chem. Int. Ed. 2012, 51, 2951
78. M. Ogasawara, S. Watanabe, K. Nakajima, T. Takahashi, J. Am. Chem. Soc. 2010, 132, 2136
79. W.-L. Duan, Y. Imazaki, R. Shintani, T. Hayashi, Tetrahedron 2007, 63, 8529
80. A. Bueno, M. Rosol, J. García, A. Moyano, Adv. Synth. Catal. 2006, 348, 2590
81. M. Ogasawara, S. Watanabe, L. Fan, K. Nakajima, T. Takahashi, Organometallics 2006, 25, 5201
82. S. Siegel, H.-G. Schmalz, Angew. Chem. 1997, 109, 2569
83. Angew. Chem. Int. Ed. Engl. 1997, 36, 2456
84. M. Uemura, H. Nishimura, T. Hayashi, J. Organomet. Chem. 1994, 473, 129
85. M. Uemura, H. Nishimura, T. Hayashi, Tetrahedron Lett. 1993, 34, 107.
86. p,R)-(+)- 3 aj ] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
87. T. Kan, T. Fukuyama, Chem. Commun. 2004, 353.
88. Chiral Ferrocenes in Asymmetric Catalysis (Eds.:, L.-X. Dai, X.-L. Hou,), Wiley-VCH, Weinheim, 2010
89. W. Chen, H.-U. Blaser, in Phosphorus Ligands in Asymmetric Catalysis, Vol.1 (Ed.:, A. Börner,), Wiley-VCH, Weinheim, 2008, chap. 4
90. H.-U. Blaser, W. Chen, F. Camponovo, A. Togni, in Ferrocenes (Ed.:, P. Štěpnička,), Wiley, Chichester, 2008, chap. 6.
91. K. Tanaka, T. Osaka, K. Noguchi, M. Hirano, Org. Lett. 2007, 9, 1307.
92. I. G. Stará, Z. Alexandrová, F. Teplý, P. Sehnal, I. Starý, D. Šaman, M. Buděšínský, J. Cvačka, Org. Lett. 2005, 7, 2547
93. P. Sehnal, Z. Krausová, F. Teplý, I. G. Stará, I. Starý, L. Rulíšek, D. Šaman, I. Císař ová, J. Org. Chem. 2008, 73, 2074
94. P. Sehnal, I. G. Stará, D. Šaman, M. Tichý, J. Míšek, J. Cvačka, L. Rulíšek, J. Chocholoušová, J. Vacek, G. Goryl, M. Szymonski, I. Císařová, I. Starý, Proc. Natl. Acad. Sci. USA 2009, 106, 13169
95. J. Žádný, A. Jančařík, A. Andronova, M. Šámal, J. V. ChocholouŠová, J. Vacek, R. Pohl, D. Šaman, I. Císařová, I. G. Stará, I. Starý, Angew. Chem. 2012, 124, 5959
96. Angew. Chem. Int. Ed. 2012, 51, 5857
97. M. R. Crittall, N. W. G. Fairhurst, D. R. Carbery, Chem. Commun. 2012, 48, 11181.
98. E. Farkas, L. Kollár, M. Moret, A. Sironi, Organometallics 1996, 15, 1345
99. L. Jánosi, L. Kollár, P. Macchi, A. Sironi, J. Organomet. Chem. 2006, 691, 2846
100. D. N. Cheredilin, F. M. Dolgushin, A. A. Korlyukov, I. A. Godovikov, R. Kadyrov, E. V. Balagurova, S. P. Solodovnikov, I. T. Chizhevsky, J. Organomet. Chem. 2006, 691, 3989.