Heteroatom radical addition-cyclization and its synthetic application

Heterocycles

Volumn 50, Issue 1, 1999, Pages 505-541

  Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SAMARIUM; SULFUR DERIVATIVE;

CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0032837567     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-98-SR(H)2     Document Type: Review

References (149)

1. (a) I. Ryu, N. Sonoda, and D. P. Curran, Chem. Rev., 1996, 96, 177;
2. (b) B. B. Snider, Chem. Rev., 1996, 96, 339;
3. (c) B. Giese, B. Kopping, T. Gobel, J. Thoma, K. J. Kulicke, and F. Track, Org. React. (N. Y.), 1996, 48, 301;
4. (d) A. G. Fallis and I. M. Brinza, Tetrahedron, 1997, 53, 17543.
5. T. Naito, Y. Honda, O. Miyata, and I. Ninomiya, J. Chem. Soc., Perkin Trans, 1, 1995, 19.
6. (a) B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press, New York, 1986;
7. (b) D. P. Curran, Synthesis, 1988, 417;
8. (c) D. P. Curran, Synthesis, 1988, 469;
9. (d) C. P. Jasperse, D. P. Curran, andT. L. Fevig, Chem. Rev., 1991, 91, 1237;
10. (e) W. B. Motherwell and D. Crick, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992;
11. (f) J. Fossy, D. Lefort, and J. Sorba, Free Radicals in Organic Chemistry, John Wiley & Sons, Inc., New York, 1995;
12. (g) D. P. Curran, N. A. Porter, and B. Giese, Stereochemistry of Radical Reactions, VCH, New York, 1996.
13. M. E. Kuehne and R. E. Damon, J. Org. Chem., 1977, 42, 1825.
14. M. E. Kuehne and W. H. Parsons, J. Org. Chem., 1977, 42, 3408.
15. T. Naito, Y. Honda, O. Miyata, and I. Ninomiya, Heterocycles, 1991, 32, 2319.
16. (a) T. Naito, Y. Honda, O. Miyata, and I. Ninomiya, Chem. Pharm. Bull., 1993, 41, 217;
17. (b) T. Naito, Y. Honda, V. Bhavakul, S. Yamaguchi, A. Fujiwara, O. Miyata, and I. Ninomiya, Chem. Pharm. Bull., 1997, 45, 1932.
18. (a) O. Miyata, A. Nishiguchi, I. Ninomiya, T. Naito, K. Aoe, and K. Okamura, Tetrahedron Lett., 1996, 37, 229;
19. (b) O. Miyata, A. Nishiguchi, I. Ninomiya, and T. Naito, Chem. Pharm. Bull., 1996, 44, 1285.
20. (a) O. Miyata, Y. Ozawa, I. Ninomiya, K. Aoe, H. Hiramatsu, and T. Naito, Heterocycles, 1997, 46, 321;
21. (b) O. Miyata, Y. Ozawa, I. Ninomiya, and T. Naito, Synlett, 1997, 275.
22. A. Padwa, H. Nimmesgern, and G. S. K. Wong, J. Org. Chem., 1985, 50, 5620.
23. A. Ogawa, R. Obayashi, H. Ine, Y. Tsuboi, N. Sonoda, and T. Hirao, J. Org. Chem., 1998, 63, 881.
24. B. Hache and Y. Gareau, Tetrahedron Lett., 1994, 35, 1837.
25. C. A. Broka and D. E. C. Reichert, Tetrahedron Lett., 1987, 28, 1503.
26. P. C. Montevecchi, M. L. Navacchia, and P. Spagnolo, Tetrahedron Lett., 1997, 38, 7913.
27. (a) T. Sugimura, S. Nagano, and A. Tai, Tetrahedron Lett., 1997, 38, 3547;
28. (b) A. J. Blake, A. R. Gladwin, G. Pattenden, and A. J. Smithies, J. Chem. Soc., PerkinTrans. 1, 1997, 1167.
29. (a) K. S. Feldman and C. J. Burns, J. Org. Chem., 1991, 56, 4601;
30. (b) K. S. Feldman, H. M. Berven, A. L. Romanelli, andM. Parvez, J. Org. Chem., 1993, 58, 6851.
31. V. H. Rawal and V. Krishnamurthy, Tetrahedron Lett., 1992, 33, 3439.
32. S. Kim and S. Lee, Tetrahedron Lett., 1991, 32, 6575.
33. S. D. Burke and K. W. Jung, Tetrahedron Lett., 1994, 35, 5837.
34. O. Miyata, K. Muroya, J. Koide, and T. Naito, Synlett, 1998, 271.
35. L. E. Kaim, A. Gacon, and A. Perroux, Tetrahedron Lett., 1998, 39, 371.
36. G. E. Keck and T. T. Wager, J. Org. Chem., 1996, 61, 8366.
37. M. D. Bachi, A. Balanov, and N. Bar-Ner, J. Org. Chem., 1994, 59, 7752.
38. T. Saegusa, S. Kobayashi, and Y. Ito, J. Org. Chem., 1970, 35, 2118.
39. (a) I. D. Riggi, J.-M. Surzur, and M. P. Bertrand, Tetrahedron, 1988, 44, 7119;
40. (b) I. D. Riggi, J.-M. Surzur, M. P. Bertrand, A. Archavlis, and R. Faure, Tetrahedron, 1990, 46, 5285;
41. (c) I. D. Riggi, R. Nouguier, J.-M. Surzur, C. Lesueur, M. P. Bertrand, C. Jaime, and A. Virgili, Bull. Soc. Chim. Fr., 1993, 130, 229;
42. (d) I. D. Riggi, S. Gastaldi, J.-M. Surzur, M. P. Bertrand, and A. Virgili, J. Org. Chem., 1992, 57, 6118;
43. (e) M.-P. Bertrand, S. Gastaldi, and R. Nouguier, Tetrahedron Lett., 1996, 37, 1229.
44. (f) R. Nouguier, C. Lesueur, E. D. Riggi, M. P. Bertrand, and A. Virgili, Tetrahedron Lett., 1990, 31, 3541.
45. (a) C.-P. Chuang, Tetrahedron, 1991, 47, 5425;
46. (b) C.-P. Chuang, S.-S. Hou, and R.-R. Wu, Synth. Commun., 1992, 22, 467.
47. A. C. Serra, C. M. M. da S. Correa, M. A. M. S. A. Vieira, and M. A. Gomes, Tetrahedron, 1990, 46, 3061.
48. S. Caddick, C. L. Shering, and S. N. Wadman, Chem. Commun., 1997, 171.
49. Y.-H. Kang and J. L. Kice, J. Org. Chem., 1984, 49, 1507.
50. (a) J. E. Brumwell, N. S. Simpkins, and N. K. Terrett, Tetrahedron, 1994, 50, 13533;
51. (b) J. E. Brumwell, N. S. Simpkins, and N. K. Terrett, Tetrahedron Lett., 1993, 34, 1219.
52. C.-P. Chuang, Synth. Commun., 1992, 22, 3151.
53. M. P. Bertrand, S. Gastaldi, and R. Nouguier, Synlett, 1997, 1420.
54. J.-M. Fang and M.-Y. Chen, Tetrahedron Lett., 1987, 28, 2853.
55. C.-P. Chuang, Tetrahedron Lett., 1992, 33, 6311.
56. (a) T. A. K. Smith and G. H. Whitham, J. Chem. Soc., Chem. Commun., 1985, 897;
57. (b) T. A. K. Smith and G. H. Whitham, J. Chem. Soc., Perkin Trans. 1, 1989, 319;
58. (c) T. A. K. Smith and G. H. Whitham, J. Chem. Soc., Perkin Trans. 1, 1989, 313;
59. (d) I. W. Harvey andG. H. Whitham, J. Chem. Soc., Perkin Trans. 1, 1993, 185;
60. (e) E. D. Phillips and G. H. Whitham, Tetrahedron Lett., 1993, 34, 2541.
61. (a) S. Hanessian and R. Leger, J. Am. Chem. Soc., 1992, 114, 3115;
62. (b) S. Hanessian and R. Leger, Synlett, 1992, 402.
63. (a) G. Stork and R. Mook, Jr., Tetrahedron Lett., 1986, 27, 4529;
64. (b) G. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1987, 109, 2829.
65. E. Lee, S. B. Ko, K. W. Jung, and M. H. Chang, Tetrahedron Lett., 1989, 30, 827;
66. (b) E. Lee, C.-U. Hur, and J.-H. Park, Tetrahedron Lett., 1989, 30, 7219;
67. (c) E. Lee, C.-U. Hur, Y. C. Jeong, Y. H. Rhee, and M. H. Chang, J. Chem. Soc., Chem. Commun., 1991, 1314;
68. (d) E. Lee, C.-U. Hur, and C. M. Park, Tetrahedron Lett., 1990, 31, 5039.
69. K. R. Biggs, P. J. Parsons, D. J. Tapolzcay, and J. M. Underwood, Tetrahedron Lett., 1989, 30, 7115.
70. N. Moufid and Y. Chapleur, Tetrahedron Lett., 1991, 32, 1799.
71. S. P. Munt and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 480.
72. D. L. Clive and H. W. Manning, J. Chem. Soc., Chem. Commun., 1993, 666.
73. K. Nozaki, K. Oshima, and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547.
74. K. Miura, K. Fugami, K. Oshima, and K. Utimoto, Tetrahedron Lett., 1988, 29, 1543.
75. S. Kim and J. S. Koh, Tetrahedron Lett., 1992, 33, 7391.
76. A. L. J. Beckwith and D. H. Roberts, J. Am. Chem. Soc., 1986, 108, 5893.
77. E. Enholm and G. Prasad, Tetrahedron Lett., 1989, 30, 4939.
78. (a) A. F. Parsons and R. M. Pettifer, Tetrahedron Lett., 1997, 38, 5907;
79. (b) A. F. Parsons and R. M. Pettifer, J. Chem. Soc., Perkin Trans. 1, 1998, 651.
80. E. Lee, J. S. Tae, Y. H. Chong, Y. C. Park, M. Yun, and S. Kim, Tetrahedron Lett., 1994, 35, 129.
81. (a) E. J. Enholm and K. S. Kinter, J. Am. Chem. Soc., 1991, 113, 7784;
82. (b) E. J. Enholm and J. A. Burroff, Tetrahedron Lett., 1992, 33, 1835.
83. D. S. Hays and G. C. Fu, J. Org. Chem., 1996, 61, 4.
84. V. H. Rawal, V. Krishnamurthy, and A. Fabre, Tetrahedron Lett., 1993, 34, 2899.
85. A. Nishida, H. Takahashi, H. Takeda, N. Takada, and O. Yonemitsu, J. Am. Chem. Soc., 1990, 112, 902.
86. T. Sygawara, B. A. Otter, and T. Ueda, Tetrahedron Lett., 1988, 29, 75.
87. Y. Yuasa, J. Ando, and S. Shibuya, J. Chem. Soc., Chem. Commun., 1994, 1383.
88. J. Ardisson, J. P. Ferezou, M. Julia, and A. Pancrazi, Tetrahedron Lett., 1987, 28, 2001.
89. E. J. Enholm, J. A. Burroff, and L. M. Jaramillo,Tetrahedron Lett., 1990, 31, 3727.
90. (a) J. M. Hatem, C. D. H.-Bernard, J. Grimaldi, and R. Maurin, Tetrahedron Lett., 1992, 33, 1057;
91. (b) C. D. B.-Henriet, J. Grimaldi, and J. M. Hatem, Tetrahedron Lett., 1994, 35, 3699;
92. J. M.-Contelles, G. Balme, D. Bouyssi, C. Destabel, C. D. H.-Bernard, J. Grimaldi, and J. M. Hatem, J. Org. Chem., 1997, 62, 1202.
93. (a) J. M.-Contelles, C. Destabel, P. Gallego, J. L. Chiara, and M. Bernabe, J. Org. Chem., 1996, 61, 1354;
94. (b) A. M.-Grau and J. M.-Contelles, Chem. Soc. Rev., 1998, 155.
95. S. Kim, I. S. Kee, and S. Lee, J. Am. Chem. Soc., 1991, 113, 9882.
96. D. Felix, R. K. Muller, U. Horn, R. Joos, J. Schreiber, and A. Eschenmoser, Helv. Chim. Acta, 1972, 55, 1276.
97. S. Kim and I. S. Kee, Tetrahedron Lett., 1993, 34, 4213.
98. J. Boivin, E. Fouquet, and S. Z. Zard, Tetrahedron Lett., 1990, 31, 3545.
99. M. D. Bachi and D. Denenmark, J. Org. Chem., 1990, 55, 3442.
100. (a) H. Pak, I. I. Canalda, and B. Fraser-Reid, J. Org. Chem., 1990, 55, 3009;
101. (b) H. Pak, J. K. Dickson, Jr., and B. Fraser-Reid, J. Org. Chem., 1989, 54, 5357.
102. D. S. Hays and G. C. Fu, J. Am. Chem. Soc., 1995, 117, 7283.
103. T. Naito, K. Tajiri, T. Harimoto, I. Ninomiya, and T. Kiguchi, Tetrahedron Lett., 1994, 35, 2205.
104. J. Tormo, D. S. Hays, and G. C. Fu, J. Org. Chem., 1998, 63, 201.
105. T. Kiguchi, K. Tajiri, I. Ninomiya, T. Naito, and H. Hiramatsu, Tetrahedron Lett., 1995, 36, 253.
106. (a) H. Miyabe, M. Torieda, T. Kiguchi, and T. Naito, Synlett, 1997, 580;
107. (b) T. Naito, M. Torieda, K. Tajiri, I. Ninomiya, and T. Kiguchi, Chem. Pharm. Bull., 1996, 44, 624.
108. (a) G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307;
109. (b) T. Skrydstrup, Angew. Chem., Int. Ed. Engl., 1997, 36, 345;
110. (c) G. A. Molander and J. A. McKie, J. Org. Chem., 1992, 57, 3132;
111. (d) G. A. Molander and S. R. Shakya, J. Org. Chem., 1996, 61, 5885.
112. D. Colclough, J. B. White, W. B. Smith, and Y. Chu, J. Org. Chem., 1993, 58, 6303.
113. (a) E. J. Enholm, H. Satici, and A. Trivellas, J. Org. Chem., 1989, 54, 5841;
114. (b) E. J. Enholm and A. Trivellas, J. Am. Chem. Soc., 1989, 111, 6463;
115. (c) E. Enholm and A. Trivellas, Tetrahedron Lett., 1994, 35, 1627.
116. J. L. Chiara, S. Martinez, and M. Bernabe, J. Org. Chem., 1996, 61, 6488.
117. (a) S. Fukuzawa, A. Nakanishi, T. Fujinami, and S. Sakai, J. Chem. Soc., Perkin Trans. 1, 1988, 1669;
118. (b) M. Kito, T. Sakai, N. Haruta, H. Nishikawa, and F. Matsuda, Synlett, 1996, 1057;
119. (c) M. Schwaebe and R. D. Little, J. Org. Chem., 1996, 61, 3240.
120. (a) J. L. Namy, J. Souppe, and H. B. Kagan, Tetrahedron Lett., 1983, 24, 765;
121. (b) J. L. Chiara, W. Cabri, and S. Hanessian, Tetrahedron Lett., 1991, 32, 1125;
122. (c) M. Adinolfi, G. Barone, A. Iadonisi, L. Mangoni, and R. Manna, Tetrahedron, 1997, 53, 11767;
123. (d) M. Adinolfi, G. Barone, A. Iadonisi, and L. Mangoni, Tetrahedron Lett., 1998, 39, 2021.
124. (a) G. A. Molander and C. Kenny, J. Org. Chem., 1991, 56, 1439;
125. (b) G. A. Molander and C. Kenny, Tetrahedron Lett., 1987, 28, 4367;
126. (c) G. A. Molander and C. Kenny, J. Am. Chem. Soc., 1989, 111, 8236;
127. (d) G. A. Molander and C. P. Losada, J. Org. Chem., 1997, 62, 2935;
128. (e) G. A. Molander and C. P. Losada, Tetrahedron, 1998, 54, 5819.
129. T. L. Fevig, R. L. Elliot, and D. P. Curran, J. Am. Chem. Soc., 1988, 110, 5064.
130. (a) R. A. Batey and W. B. Motherwell, Tetrahedron Lett., 1991, 32, 6649;
131. (b) C. Anies, J.-Y. Lallemand, and A. Pancrazi, Tetrahedron Lett., 1996, 37, 5523.
132. S. F. Martin, C.-P. Yang, W. L. Laswell, and H. Rueger, Tetrahedron Lett., 1988, 29, 6685.
133. (a) J. M.-Contelles, P. Gallego, M. R.-Fernandez, N. Khiar, C. Destabel, M. Bernabe, A. M.-Grau, and J. L. Chiara, J. Org. Chem., 1997, 62, 7397;
134. (b) H. Miyabe, S. Kanehira, K. Kume, H. Kandori, and T. Naito, Tetrahedron, 1998, 54, 5883.
135. (a) C. F. Sturino and A. G. Fallis, J. Am. Chem. Soc., 1994, 116, 7447;
136. (b) C. F. Sturino and A. G. Fallis, J. Org. Chem., 1994, 59, 6514.
137. G. A. Molander and C. R. Harris, Tetrahedron, 1998, 54, 3321.
138. E. J. Corey and S. G. Pyne, Tetrahedron Lett., 1983, 24, 2821.
139. P. Hegarty and J. Mann, Tetrahedron, 1995, 51, 9079.
140. G. A. Kraus and S. Liras, Tetrahedron Lett., 1990, 31, 5265.
141. K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1992, 2477.
142. K. J. Kulicke, C. Chatgilialoglu, B. Kopping, and B. Giese, Helv. Chim. Acta, 1992, 75, 935.
143. I. Ojima, R. J. Donovan, and W. R. Shay, J. Am. Chem. Soc., 1992, 114, 6580.
144. G. J. Hollingworth, G. Pattenden, and D. J. Schulz, Aust. J. Chem., 1995, 48, 381.
145. (a) T. Kataoka, M. Yoshimatsu, H. Shimizu, and M. Hori, Tetrahedron Lett., 1990, 31, 5927;
146. (b) T. Kataoka, M. Yoshimatsu, Y. Noda, T. Sato, H. Shimizu, and M. Hori, J. Chem. Soc., Perkin Trans. 1, 1993, 121.
147. A. Ogawa, H. Yokoyama, K. Yokoyama, T. Masawaki, N. Kambe, and N. Sonoda, J. Org. Chem., 1991, 56, 5721.
148. J. E. Brumwell, N. S. Simpkins, and N. K. Terrett, Tetrahedron Lett., 1993, 34, 1215.
149. A. J. Bloodworth, R. J. Curtis, and N. Misery, J. Chem. Soc., Perkin Trans, 1, 1989, 954.