Asymmetric Synthesis of Six-Membered Ring Heterocycles

Asymmetric Synthesis of Nitrogen Heterocycles

Volumn , Issue , 2009, Pages 95-138

  Toyooka, Naoki ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Asymmetric synthesis; Dihydropyridines; Piperidine; Six membered ring heterocycles; Tetrahydropyridines

Indexed keywords

EID: 84878247742     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527625505.ch3     Document Type: Chapter

References (101)

1. Bailey, P. D., Millwood, P. A. and Smith, P. D. (1998) Chem. Commun., 633-40;
2. Weinstraub, P. M., Sabol, J. S., Kane, J. M. and Borcherding, D. R. (2003) Tetrahedron, 59, 2953-89;
3. Buffat, M. G. P. (2004) Tetrahedron, 60, 1701-29;
4. Laschat, S. and Dickner, T. (2000) Synthesis, 1781-813.
5. Comins, D. L. and Joseph, S. P. (1996) Adv. Nitrogen Heterocycl., 2, 251-94.
6. Charette, A. B., Grenon, M., Lemire, A., Pourashraf, M. and Martel, J. (2001) J. Am. Chem. Soc., 123, 11829-30.
7. Lemire, A. and Charette, A. B. (2005) Org. Lett., 7, 2747-50.
8. Ichikawa, E., Suzuki, M., Yabu, K., Albert, M., Kanai, M. and Shibasaki, M. (2004) J. Am. Chem. Soc., 126, 11808-9.
9. Sun, Z., Yu, S., Ding, Z. and Ma, D. (2007) J. Am. Chem. Soc., 129, 9300-1.
10. Yamada, S. and Morita, C. (2002) J. Am. Chem. Soc., 124, 8184-85.
11. Kuethe, J. T. and Comins, D. L. (2000) Org. Lett., 2, 855-57;
12. Kuethe, J. T. and Comins, D. L. (2004) J. Org. Chem., 69, 5219-31.
13. Comins, D. L., Huang, S., McArdle, C. L. and Ingalls, C. L. (2001) Org. Lett., 3, 469-71.
14. Comins, D. L. and Williams, A. L. (2000) Tetrahedron Lett, 41, 2839-42.
15. Gotchev, D. B. and Comins, D. L. (2006) J. Org. Chem, 71, 9393-402.
16. Felpin, F.-X. and Lebreton, J. (2003) Eur. J. Org. Chem, 3693-712.
17. Davis, F. A., Zhang, Y. and Li, D. (2007) Tetrahedron Lett., 48, 7838-40.
18. Felpin, F.-X., Boubekeur, K. and Lebreton, J. (2003) Eur. J. Org. Chem., 4518-27.
19. Lee, H. K., Im, J. H. and Jung, S. H. (2007) Tetrahedron, 63, 3321-27.
20. Holub, N., Neidhofer, J. and Blechert, S. (2005) Org. Lett., 7, 1227-29.
21. Rueping, M. and Antonchick, A. P. (2007) Angew. Chem. Int. Ed., 46, 4562-65.
22. Takahata, H., Suto, Y., Kato, E., Yoshimura, Y. and Ouchi, H. (2007) Adv. Synth. Catal., 349, 685-93.
23. Ouchi, H., Mihara, Y. and Takahata, H. (2005) J. Org. Chem, 70, 5207-14.
24. Montoro, R., Marquez, F., Llebaria, A. and Delgado, A. (2003) Eur. J. Org. Chem, 217-23.
25. Davis, F. A., Xu, H. and Zhang, J. (2007) J. Org. Chem, 72, 2046-52.
26. Pu, X. and Ma, D. (2003) J. Org. Chem, 68, 4400-5.
27. Ma, N. and Ma, D. (2003) Tetrahedron: Asymmetry, 14, 1403-6.
28. Ma, D. and Ma, N. (2003) Tetrahedron Lett., 44, 3963-65.
29. Davies, S. G. and Ichihara, O. (1991) Tetrahedron: Asymmetry, 2, 183-86.
30. Garraffo, H. M., Jain, P., Spande, T. F. and Daly, J. W. (1997) J. Nat. Prod., 60, 2-5.
31. Yu, S., Zhu, W. and Ma, D. (2005) J. Org. Chem., 70, 7364-70.
32. Pu, X. and Ma, D. (2004) Angew. Chem. Int. Ed., 43, 4222-25.
33. Pu, X. and Ma, D. (2006) J. Org. Chem., 71, 6562-72.
34. Tanaka, K. and Katsumura, S. (2002) J. Am. Chem. Soc., 124, 9660-61.
35. Kobayashi, T., Nakashima, M., Hakogi, T., Tanaka, K. and Katsumura, S. (2006) Org. Lett., 8, 3809-12.
36. Kobayashi, T., Hasegawa, F., Tanaka, K. and Katsumura, S. (2006) Org. Lett., 8, 3813-16.
37. Wurz, R. P. and Fu, G. C. (2005) J. Am. Chem. Soc., 127, 12234-35.
38. Cossy, J., Willis, C., Bellosta, V. and BouzBouz, S. (2002) J. Org. Chem., 67, 1982-92.
39. Takahata, H., Ouchi, H., Ichinose, M. and Nemoto, H. (2002) Org. Lett., 4, 3459-62.
40. Concello'n, J. M., Riego, E., Rivero, I. A. and Ochoa, A. (2004) J. Org. Chem., 69, 6244-48.
41. Eskici, M. and Gallagher, T. (2000) Synlett, 1360-62.
42. Masuda, Y., Tashiro, T. and Mori, K. (2006) Tetrahedron: Asymmetry, 17, 3380-85.
43. Kandula, S. R. V. and Kumar, P. (2006) Tetrahedron, 62, 9942-48.
44. Singh, R. and Ghosh, S. K. (2002) Tetrahedron Lett, 43, 7711-15.
45. Lee, Y.-S., Shin, Y.-H., Kim, Y.-H., Lee, K.-Y., Oh, C.-Y., Pyun, S.-J., Park, H.-J., Jeong, J.-H. and Ham, W.-H. (2003) Tetrahedron: Asymmetry, 14, 87-93.
46. Enders, D. and Kirchhoff, J. H. (2000) Synthesis, 2099-105.
47. Yokoyama, H., Otaya, K., Kobayashi, H., Miyazawa, M., Yamaguchi, S. and Hirai, Y. (2000) Org. Lett., 2, 2427-29.
48. Yokoyama, H., Ejiri, H., Miyazawa, M., Yamaguchi, S. and Hirai, Y. (2007) Tetrahedron: Asymmetry, 18, 852-56.
49. Hirai, Y., Watanabe, J., Nozaki, T., Yokoyama, H. and Yamaguchi, S. (1997) J. Org. Chem., 62, 776-77.
50. Makabe, H., Kong, L. K. and Hirota, M. (2003) Org. Lett., 5, 27-29.
51. Welter, C., Dahnz, A., Brunner, B., Streiff, S., Dulbon, P. and Helmchen, G. (2005) Org. Lett., 7, 1239-42.
52. LaLonde, R. L., Sherry, B. D., Kang, E. J. and Toste, F. D. (2007) J. Am. Chem. Soc., 129, 2452-53.
53. Abrunhosa-Thomas, I., Roy, O., Barra, M., Besset, T., Chalard, P. and Troin, Y. (2007) Synlett, 1613-15.
54. Kawabata, T., Kawakami, S. and Majumdar, S. (2003) J. Am. Chem. Soc., 125, 13012-13.
55. Davis, F. A. and Yang, B. (2005) J. Am. Chem. Soc., 127, 8398-407.
56. Davis, F. A. and Santhanaraman, M. (2006) J. Org. Chem., 71, 4222-26.
57. Davis, F. A., Chao, B. and Rao, A. (2001) Org. Lett., 3, 3169-71.
58. Monfray, J., Gelas-Mialhe, Y., Gramain, J.-C. and Remuson, R. (2005) Tetrahedron: Asymmetry, 16, 1025-34.
59. Kinderman, S. S., de Gelder, R., van Maarseveen, J. H., Schoemaker, H. E., Hiemstra, H. and Rutjes, F. P. J. T. (2004) J. Am. Chem. Soc., 126, 4100-1.
60. Huang, H., Spande, T. F. and Panek, J. S. (2003) J. Am. Chem. Soc., 125, 626-27.
61. Glasson, S. R., Canet, J.-L. and Troin, Y. (2000) Tetrahedron Lett., 41, 9797-802.
62. Carbonnel, S., Fayet, C., Gelas, J. and Troin, Y. (2000) Tetrahedron Lett., 41, 8293-96.
63. Ciblat, S., Calinaud, P., Canet, J.-L. and Troin, Y. (2000) J. Chem. Soc. Perkin Trans. 1, 353-57.
64. Gandon, L. A., Russell, A. G., Güveli, T., Brodwolf, A. E., Kariuki, B. M., Spencer, N. and Snaith, J. S. (2006) J. Org. Chem., 71, 5198-207.
65. Tour, B. B. and Hall, D. G. (2004) Angew. Chem. Int. Ed., 43, 2001-4.
66. Ozawa, T., Aoyagi, S. and Kibayashi, C. (2000) Org. Lett., 2, 2955-58.
67. Ozawa, T., Aoyagi, S. and Kibayashi, C. (2001) J. Org. Chem., 66, 3338-47.
68. Sato, T., Aoyagi, S. and Kibayashi, C. (2003) Org. Lett., 5, 3839-42.
69. Adelbrecht, J.-C., Craig, D., Fleming, A. J. and Martin, F. M. (2005) Synlett, 2643-47.
70. Tan, C.-H. and Holmes, A. B. (2001) Chem. Eur. J., 7, 1845-54.
71. Cossy, J., Mirguet, O., Pardo, D. G. and Desmurs, J.-R. (2001) Tetrahedron Lett., 42, 5705-7.
72. Lee, J., Hoang, T., Lewis, S., Weissman, S. A., Askin, D., Volante, R. P. and Reider, P. J. (2001) Tetrahedron Lett., 42, 6223-25.
73. Lonkar, P. S. and Kumar, V. A. (2004) Bioorg. Med. Chem. Lett., 14, 2147-49.
74. Honda, T. and Kimura, M. (2000) Org. Lett., 2, 3925-27.
75. Heller, E., Lautenschläger, W. and Holzgrabe, U. (2005) Tetrahedron Lett., 46, 1247-49.
76. Langlois, N. (2002) Org. Lett, 4, 185-87.
77. Poupon, E., François, D., Kunesch, N. and Husson, H.-P. (2004) J. Org. Chem., 69, 3836-41.
78. Francois, D., Poupon, E., Kunesch, N. and Husson, H.-P. (2004) Eur. J. Org. Chem., 4823-29.
79. Roulland, E., Cecchin, F. and Husson, H.-P. (2005) J. Org. Chem., 70, 4474-77.
80. Roulland, E., Chiaroni, A. and Husson, H.-P. (2005) Tetrahedron Lett., 46, 4065-68.
81. Calvet-Vitale, S., Vanucci-Bacque, C., Fargeau-Bellassoued, M.-C. and Lhommet, G. (2005) Tetrahedron, 61, 7774-82.
82. Noël, R., Vanucci-Bacqué, C., Fargeau-Bellassoued, M.-C. and Lhommet, G. (2007) Eur. J. Org. Chem., 476-86.
83. Amat, M., Llor, N., Hidalgo, J., Escolano, C. and Bosch, J. (2003) J. Org. Chem., 68, 1919-28.
84. Amat, M., Lozano, O., Escolano, C., Molins, E. and Bosch, J. (2007) J. Org. Chem., 72, 4431-39.
85. Toyooka, N., Fukutome, A., Nemoto, H., Daly, J. W., Spande, T. F., Garraffo, H. M. and Kaneko, T. (2002) Org. Lett., 4, 1715-18.
86. Toyooka, N., Fukutome, A., Shinoda, H. and Nemoto, H. (2004) Tetrahedron, 60, 6197-216.
87. Toyooka, N., Fukutome, A., Shinoda, H. and Nemoto, H. (2003) Angew. Chem. Int. Ed., 42, 3808-10.
88. Ashoorzadeh, A. and Caprio, V. (2005) Synlett, 346-48.
89. Itoh, T., Yamazaki, N. and Kibayashi, C. (2002) Org. Lett., 4, 2469-72.
90. Myers, E. L., de Vries, J. G. and Aggarwal, V. K. (2007) Angew. Chem. Int. Ed., 46, 1893-96.
91. Wijdeven, M. A., Botman, P. N. M., Wijtmans, R., Schoemaker, H. E., Rutjes, F. P. J. T. and Blaauw, R. H. (2005) Org. Lett., 7, 4005-7.
92. Huang, P.-Q., Guo, Z.-Q. and Ruan, Y.-P. (2006) Org. Lett., 8, 1435-38.
93. Liu, L.-X., Ruan, Y.-P., Guo, Z.-Q. and Huang, P.-Q. (2004) J. Org. Chem., 69, 6001-9.
94. Huang, P.-Q., Liu, L.-X., Wei, B.-G. and Ruan, Y.-P. (2003) Org. Lett., 5, 1927-29.
95. Furukubo, S., Moriyama, N., Onomura, O. and Matsumura, Y. (2004) Tetrahedron Lett, 45, 8177-81.
96. Turcaud, S., Sierecki, E., Martens, T. and Royer, J. (2007) J. Org. Chem, 72, 4882-85.
97. Smith, A. B. and Kim, D.-S. III (2005) Org. Lett, 7, 3247-50.
98. Smith, A. B. and Kim, D.-S. III (2006) J. Org. Chem, 71, 2547-57.
99. Yu, S., Pu, X., Cheng, T., Wang, R. and Ma, D. (2006) Org. Lett., 8, 3179-82.
100. Angle, S. R., Qian, X. L., Pletnev, A. A. and Chinn, J. (2007) J. Org. Chem, 72, 2015-20.
101. Wei, L.-L., Hsung, R. P., Sklenicka, H. M. and Gerasyuto, A. I. (2001) Angew. Chem. Int. Ed., 40, 1516-18.