Development of synthetic methods with indium

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 67, Issue 3, 2009, Pages 239-247

  Yanada, Reiko ^a   Takemoto, Yoshiji ^b  

^a HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Alkylideneoxin dole; Alkyne; Atom transfer and reductive cyclization; Dihy droisoquinoline; Indium (0); Indium (III); Lewis acid; Radical cyclization; Stereoselective synthesis; Tandem reaction

Indexed keywords

FREE RADICAL REACTIONS; INDIUM; IONIZATION POTENTIAL; STEREOCHEMISTRY; STEREOSELECTIVITY;

ALKYLIDENEOXIN- DOLE; ALKYNE; DIHY- DROISOQUINOLINE; LEWIS ACID; RADICAL CYCLIZATIONS; REDUCTIVE CYCLIZATION; STEREOSELECTIVE SYNTHESIS; TANDEM REACTION;

CYCLIZATION;

EID: 67650021596     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.67.239     Document Type: Article

References (65)

1. (a) L. A. Paquette, In Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes; P. T. Anastas, T. C. Williamson, eds.; Oxford University Press: New York, 1998;
2. (b) P. C. Andrews, A. C. Peatt, C. L. Raston, Green Chem., 6, 119 (2004) ;
3. (c) M. Pham, A. Allatabakhsh, T. G. Minehan, J. Org. Chem., 73, 741 (2008)
4. M. Yasuda, J. Synth. Org. Chem., Jpn., 65, 99 (2007)
5. R. Yanada, A. Kaieda, Y. Takemoto, J. Org. Chem., 66, 7516 (2001)
6. (a) R. A. Fernandes, A. Stimac, Y. Yamamoto, J. Am. Chem. Soc., 125, 14133 (2003) ;
7. (b) F. Colombo, R. Annunziata, M. Benaglia, Tetrahedron Lett., 48, 2687 (2007)
8. (a) M. D. Chappell, R. L. Halcomb, Org. Lett., 2, 2003 (2000) ;
9. (b) T.-P. Loh, G.-L. Chua, J. Synth. Org. Chem., Jpn., 63, 1137 (2005) ;
10. (c) K. Zheng, B. Qin, X. Liu, X. Feng, J. Org. Chem., 72, 8478 (2007)
11. (a) N. Negoro, R. Yanada, M. Okaniwa, K. Yanada, T. Fujita, Synlett., 1998, 835;
12. (b) R. Yanada, N. Negoro, M. Okaniwa, T. Ibuka, Tetrahedron, 55, 13947 (1999) ;
13. (c) R. Yanada, N. Negoro, M. Okaniwa, Y. Miwa, T. Taga, K. Yanada, T. Fujita, Synlett., 1999, 537;
14. (d) R. Yanada, T. Ibuka, J. Synth. Org. Chem., Jpn., 58, 597 (2000) ;
15. (e) R. Yanada, M. Okaniwa, A. Kaieda, T. Ibuka, Y. Takemoto, J. Org. Chem., 66, 1283 (2001)
16. (Japaesse Source)
17. S. Araki, T. Kamei, T. Hirashita, H. Yamamura, M. Kawai, Org. Lett., 2, 847 (2000)
18. (a) R. Yanada, N. Nishimori, A. Matsumura, N. Fujii, Y. Take- moto, Tetrahedron Lett., 43, 4585 (2002) ;
19. (b) R. Yanada, Y. Koh, N. Nishimori, A. Matsumura, S. Obika, H. Mitsuya, N. Fujii, Y. Takemoto, J. Org. Chem., 69, 2417 (2004)
20. 2: D. P. Curran, M. J. Totleben, J. Am. Chem. Soc., 114, 6050 (1992) ;
21. (b) Cobaloxime: K. Wakabayashi, H. Yorimitsu, K. Oshima, ibid., 123, 5374 (2001) ;
22. 2 + Grignard reagent: S. Nii, J. Terao, N. Kambe, J. Org. Chem., 65, 5291 (2000) ;
23. 2: S. Mikami, K. Fujita, T. Nakamura. H. Yorimitsu, H. Shinokubo, S. Matsubara, K. Oshima, Org. Lett., 3, 1853 (2001) ;
24. 2Zr (H) Cl: K. Fujita, T. Nakamura, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc., 123, 3137 (2001) ;
25. (f) Cyclohexadienyl-silane: A. Studer, S. Amrein, Angew. Chem. Int. ed., 39, 3080 (2000)
26. D. P. Curran, M.-H. Chen, D. Kim, J. Am. Chem. Soc., 111, 6265 (1989)
27. K. Takami, H. Yorimitsu, H. Shinokubo, S. Matsubara, K. Oshima, Org. Lett., 3, 1997 (2001)
28. R. Yanada, S. Obika, N. Nishimori, M. Yamaguchi, Y. Take- moto, Tetrahedron Lett., 45, 2331 (2004)
29. (a) D. L. Boger, S. R. Brunette, R. M. Garbaccio, J. Org. Chem., 66, 5163 (2001) ;
30. (b) D. L. Boger, H. W. Schmitt, B. E. Fink, M. P. Hedrick, ibid., 66, 6654 (2001)
31. (a) R. Yanada, S. Obika, M. Oyama, Y. Takemoto, Org. Lett., 6, 2825 (2004) ;
32. (b) R. Yanada, S. Obika, Y. Kobayashi, T. Inokuma, M. Oyama, K. Yanada, Y. Takemoto, Adv. Synth. Cat., 347, 1632 (2005)
33. (a) L. Sun, C. Liang, S. Shirazian, Y. Zhou, T. Miller, J. Cui, J. Y. Fukuda, J.-Y. Chu, A. Nematalla, X. Wang, H. Chen, A. Sistla, T. C. Luu, F. Tang, J. Wei, C. Tang, J. Med. Chem., 46, 1116 (2003) ;
34. (b) S. Lin, Z.-Q. Yang, B. H. B. Kwok, M. Koldobskiy, C. M. Crews, S. J. Danishefsky, J. Am. Chem. Soc., 126, 6347 (2004)
35. R. Callaghan, C. F. Higgins, Brit. J. Cancer, 71, 294 (1995)
36. M. R. Fielding, R. Grigg, C. J. Urch, Chem. Commun., 2000, 2239
37. S. A. Brunton, K. Jones, J. Chem. Soc., Perkin Trans 1, 2000, 763
38. K. Inoue, A. Sawada, I. Shibata, A. Baba, J. Am. Chem. Soc., 124, 906 (2002)
39. S. P. H. Mee, V. Lee, J. E. Baldwin, Angew. Chem. Int. ed., 43, 1132 (2004)
40. (a) K. Takami, H. Yorimitsu, K. Oshima, Org. Lett., 4, 2993 (2002) ;
41. (b) T. Hirashita, Y. Hayashi, K. Mitsui, S. Araki, J. Org. Chem., 68, 1309 (2003)
42. (a) R. Yanada, S. Obika, H. Kono, Y. Takemoto, Angew. Chem. Int. ed., 45, 3822 (2006) ;
43. (b) S. Obika, H. Kono, Y. Yasui, R. Yanada, Y. Takemoto, J. Org. Chem., 72, 4462 (2007)
44. (a) J. Chen, X. Chen, M. Bois-Choussy, J. Zhu, J. Am. Chem. Soc., 128, 87 (2006) ;
45. (b) A. M. Taylor, S. L. Schreiber, Org. Lett., 8, 143 (2006) ;
46. (c) S. Zheng, C. Chan, T. Furuuchi, B. J. D. Wright, B. Zhou, J. Guo, S. J. Danishefsky, Angew. Chem., Int. ed., 45, 1754 (2006) ;
47. (d) G. Vincent, R. M. Williams, ibid., 46, 1517 (2007)
48. (a) M. Nakamura, K. Endo, E. Nakamura, J. Am. Chem. Soc., 125, 13002 (2003) ;
49. (b) N. Sakai, K. Annaka, T. Konakahara, Org. Lett., 6, 1527 (2004) ;
50. (c) T. Tsuchimoto, H. Matsubayashi, M. Kaneko, E. Shirakawa, Y. Kawakami, Angew. Chem. Int. ed., 44, 1336 (2005) ;
51. (d) M. Weïwer, L. Coulombel, E. Duñach, Chem. Commun., 2006 332;
52. (e) T. Tsuchimoto, J. Synth. Org. Chem., Jpn., 64, 752 (2006)
53. (a) R. Takita, Y. Fukuta, R. Tsuji, T. Ohshima, M. Shibasaki, Org. Lett., 7, 1363 (2005) ;
54. (b) N. Sakai, R. Kanada, M. Hirasawa, T. Konakahara, Tetrahedron, 61, 9298 (2005) ;
55. (c) R. Takita, K. Yakura, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 127, 13760 (2005)
56. R. Yanada, K. Hashimoto, R. Tokizane, Y. Miwa, H. Minami, K. Yanada, M. Ishikura, Y. Takemoto, J. Org. Chem., 73, 5135 (2008)
57. (a) N. Asao, K. Iso, S. S. Yudha, Org. Lett., 8, 4149 (2006) ;
58. (b) S. Su, J. A. Jr., Porco, J. Am. Chem. Soc., 129, 7744 (2007)
59. (a) N. Asao, T. Nogami, K. Takahashi, Y. Yamamoto, J. Am. Chem. Soc., 124, 764 (2002) ;
60. (b) J. Barluenga, H. Vázquez-Villa, A. Ballesteros, J. M. González, J. Am. Chem. Soc., 125, 9028 (2003)
61. (a) N. Asao, K. Sato, Menggenbateer, Y. Yamamoto, J. Org. Chem., 70, 3682 (2005) ;
62. (b) N. Asao, K. Sato, Org. Lett., 8, 5361 (2006) ;
63. (c) H. Kusama, H. Funami, N. Iwasawa, Synthe- sis, 2007, 2014
64. (a) G. Hilt, W. Hess, F. Schmidt, Eur. J. Org. Chem., 2526 (2005) ;
65. (b) W.-G. Shou, Y.-Y. Yang, Y.-G. Wang, J. Org. Chem., 71, 9241 (2006)