Electrophile mediated heteroatom cyclizations onto C-C π-Bonds. Part 2: Metal ion mediated cyclization

Organic Preparations and Procedures International

Volumn 29, Issue 1, 1997, Pages 63-115

  Frederickson, Martyn ^a   Grigg, Ronald ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

METAL IONS;

CYCLIZATIONS; ELECTROPHILES; HETEROATOMS; METALS IONS;

CYCLIZATION;

EID: 0011749998     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304949709355173     Document Type: Article

References (154)

1. V. I. Staninets and E. A. Shilov, Russ. Chem. Rev. (Engl. Transl.), 40, 272 (1971).
2. M. D. Dowle and D. I. Davies, Chem. Soc. Rev., 8, 171 (1979).
3. P. A. Bartlett, Tetrahedron, 36, 2 (1980).
4. P. A. Bartlett, in Asymmetric Synthesis, Vol. 3, p. 411, Academic Press, New York, 1984.
5. G. Cardillo and M. Orena, Tetrahedron, 46, 3321 (1990).
6. L. S. Hegedus, in The Chemistry of the Metal-Carbon Bond, Vol. 2, p. 401, John Wiley and Sons Ltd., New York, 1985.
7. L. S. Hegedus, in Comprehensive Organic Synthesis, Vol. 4, p. 551, Pergamon Press, Oxford, 1991.
8. I. Ishikawa, V. E. Khachatrian, R. G. Melik-Ohanjanian, N. Kawahara, Y. Mizuno and H. Ogura, Chem. Pharm. Bull. Jpn., 40, 846 (1992)
9. C. H. Heathcock, J. A. Stafford and D. L. Clark, J. Org. Chem., 57, 2575 (1992).
10. K. D. Raner and A. D. Ward, Australian J. Chem., 44, 1749 (1991).
11. K. C. Majumdar, R. N. De and S. Saha, Tetrahedron Lett., 31, 1207 (1990).
12. V. N. Kallinin, S. K. Moiseev, V. I. Bakhmutov and I. A. Cherepanov, J. Organomet. Chem., 383, 85 (1990).
13. X. Bai, S. W. Mascarella, W. D. Bowen and F. I. Carroll, Chem. Commun., 2401 (1994).
14. A. Dehghani, X. Bai, S. W. Mascarella, W. D. Bowen and F. I. Carroll, Tetrahedron Lett., 35, 8969 (1994).
15. M. K. Tong, E. M. Blumenthal and B. Ganem, Tetrahedron Lett., 31, 1683 (1990).
16. N. Chida, K. Sugihara and S. Ogawa, Chem. Commun., 901 (1994).
17. F. Le Moigne, A. Mercier and P. Tordo, Tetrahedron Lett., 32, 3841 (1991).
18. P. Stipa, J.-P. Finet, F. Le Moigne and P. Tordo, J. Org. Chem., 58, 4465 (1993).
19. F. Le Moigne and P. Tordo, J. Org. Chem., 59, 3365 (1994).
20. J. Barluenga, F. Aznar, S. Fraiz Jr. and A. Pinto, Tetrahedron Lett., 32, 3205 (1991).
21. J.-E. Bäckvall and P. G. Anderson, J. Am. Chem. Soc., 112, 3683 (1990).
22. P. G. Anderson and A. Aranyos, Tetrahedron Lett., 35, 4441 (1994).
23. M. Rönn, J.-E. Bäckvall and P. H. Andersson, Tetrahedron Lett., 36, 7749 (1995).
24. J.-E. Bäckvall, P. G. Anderson, G. B. Stone and A. Gogoll, J. Org. Chem., 56, 2988 (1991).
25. P. G. Anderson and J.-E. Bäckvall, J. Am. Chem. Soc., 114, 8696 (1992).
26. J.-E. Bäckvall, Pure Appl. Chem., 64, 429 (1992).
27. S. Igarashi, Y. Haruta, M. Ozawa, Y. Nishide, H. Kinoshita and K. Inomata, Chemistry Lett., 737 (1989).
28. V. Jäger and W. Hümmer, Angew. Chem., Intl. Ed. Engl., 29, 1171 (1990).
29. H. Takahata, Y. Banba and T. Momose, Tetrahedron:Asymmetry, 2, 445 (1991).
30. Y. Tamaru, H. Tanigawa, S. Itoh, M. Kimura, S. Tanaka, K. Fugami, T. Sekiyama and Z.-I. Yoshida, Tetrahedron Lett., 33, 631 (1992).
31. M. C. Desai and S. L. Lefkowitz, Tetrahedron Lett., 35, 4701 (1994).
32. T. Yamakazi, R. Gimi and J. T. Welch, Synlett, 573 (1991).
33. M. S. Chorghade, C. T. Cseke and P. S. Liu, Tetrahedron: Asymmetry, 5, 2251 (1994).
34. D. R. Adams, W. Carruthers, M. J. Williams and P. J. Crowley, J. Chem. Soc., Perkin Trans. 1, 1507 (1989).
35. H. Takahata, H. Takehara, N. Ohkubo and T. Momose, Tetrahedron: Asymmetry, 1, 561 (1990).
36. H. Takahata, M. Tajima, Y. Banba and T. Momose, Chem. Pharm. Bull. Jpn., 37, 2550 (1989).
37. H. Takahata, Y. Banba and T. Momose, Tetrahedron: Asymmetry, 1, 763 (1990).
38. H. Takahata, Y. Banba, M. Tajima and T. Momose, J. Org. Chem., 56, 240 (1991).
39. H. Takahata, Y. Banba and T. Momose, Tetrahedron, 47, 7635 (1991).
40. H. Takahata, H. Bandoh and T. Momose, Tetrahedron: Asymmetry, 2, 351 (1991).
41. H. Takahata, H. Bandoh and T. Momose, J. Org. Chem., 57, 4401 (1992).
42. H. Takahata, H. Bandoh, M. Hanayama and T. Momose, Tetrahedron: Asymmetry, 3, 607(1992).
43. H. Takahata, H. Bandoh and T. Momose, Tetrahedron, 49, 11205 (1993).
44. R. Amoroso, G. Cardillo and C. Tomasini, Tetrahedron Lett., 31, 6413 (1990).
45. R. Amoroso, G. Cardillo and C. Tomasini, Tetrahedron Lett., 32, 1971 (1991).
46. R. Amoroso, G. Cardillo, C. Tomasini and P. Tortoreto, J. Org. Chem., 57, 1082 (1992).
47. K. E. Harding and M. W. Jones, Heterocycles, 28, 663 (1989).
48. J. M. Takacs, M. A. Helle and L. Yang, Tetrahedron Lett., 30, 1777 (1989).
49. J. M. Takacs, M. A. Helle and F. Takusagawa, Tetrahedron Lett., 30, 7321 (1989).
50. J. M. Takacs, M. A. Helle, B. J. Sanyal and T. A. Eberspacher, Tetrahedron Lett., 31, 6765 (1990).
51. K. E. Harding, D. R. Hollingsworth and J. Reibenspies, Tetrahedron Lett., 30, 4775 (1989).
52. M. Frederickson, R. Grigg, J. Markandu and J. Redpath, Chetn. Commun., 2225 (1994).
53. R. Grigg, M. Hadjisoteriou, P. Kennewell, J. Markandu and M. Thomton-Pett, Tetrahedron Lett., 1388 (1992).
54. M. F. Semmelhack and N. Zhang, J. Org. Chem., 54, 4483 (1989).
55. M. F. Semmelhack, C. R. Kim, W. Dobler and M. Meier, Tetrahedron Lett., 30, 4925 (1989).
56. M. F. Semmelhack, C. R. Kim, N. Zhang, C. Bodurow, M. Sanner, W. Dobler and M. Meier, Pure Appi. Chem., 62, 2035 (1990).
57. M. F. Semmelhack and W. R. Epa, Tetrahedron Lett., 34, 7205 (1993).
58. M. F. Semmelhack, W. R. Epa, W.-H. Cheung, Y. Gu, C. Kim, N. Zhang and W. Lew, J. Am. Chem. Soc., 116, 7455 (1994).
59. M. McCormick, R. Monahan III, J. Soria, D. Goldsmith and D. Liotta, J. Org. Chem., 54, 4485 (1989).
60. J.-E. Bäckvall and P. G. Andersson, J. Am. Chem. Soc., 114, 6374 (1992).
61. J.-E. Bäckvall and P. G. Andersson, J. Org. Chem., 56, 2274 (1991).
62. P. G. Andersson, Y. I. M. Nilsson and J.-E. Bäckvall, Tetrahedron, 50, 559 (1994).
63. P. G. Andersson and J.-E. Bäckvall, J. Org. Chem., 56, 5349 (1991).
64. E. B. Koroleva, J.-E. Bäckvall and P. G. Andersson, Tetrahedron Lett., 36, 5397 (1995).
65. T. Hosokawa, T. Kono, T. Shinohara and S.-I. Murahashi, J. Organomet. Chem., 370, C13 (1989).
66. T. Hosokawa and S.-I. Murahashi, Acc. Chem. Res., 23, 49 (1990).
67. T. Hosokawa, F. Nakajima, S. Iwasa and S.-I. Murahashi, Chemistry Lett., 1387 (1990).
68. T. Hosokawa and S.-I. Murahashi, Heterocycles, 33, 1079 (1992).
69. R. J. Kumar, G. L. D. Krupadanam and G. Srimannnarayana, Synthesis, 535 (1990).
70. T. Gracza, T. Hasenöhrl, U. Stahl and V. Jäger, Synthesis, 1108 (1991).
71. T. Gracza and V. Jäger, Synlett, 191 (1992).
72. T. Gracza and V. Jäger, Synthesis, 1359 (1994).
73. C. P. Holmes and P. A. Bartlett, J. Org. Chem., 54, 98 (1989).
74. G. A. Kraus, J. Li, M. S. Gordon and J. H. Jensen, J. Org. Chem., 60, 1154 (1995).
75. F. Freeman and K. D. Robarge, J. Org. Chem., 54, 346 (1989).
76. O. Andrey and Y. Landais, Tetrahedron Lett., 34, 8435 (1993).
77. A. Garavelas, I. Mavropoulos, P. Perlmutter and G. Westman, Tetrahedron Lett., 36, 463 (1995).
78. P. Kocovsky, Organometallics, 12, 1969 (1993).
79. A. P. Kozikowski and J. Lee, J. Org. Chem., 55, 863 (1990).
80. N. J. Newcombe, R. J. Vijn and W. N. Speckamp, Chem. Commun., 767 (1994).
81. W. N Speckamp, N. J. Newcombe, H. Hiemstra, F. Ya, R. J. Vijn and W.-J. Koot, Pure Appl. Chem., 66, 2163 (1994).
82. H. J. M. Gijsen, J. B. P. A. Wijnberg, G. A. Stork and A. de Groot, Tetrahedron, Al, 4409 (1991).
83. M. A. Avery, P. Fan, J. M. Karle, R. Miller and K. Goins, Tetrahedron Lett., 36, 3965 (1995).
84. G. A. Kraus and J. Li, Synlett, 525 (1993).
85. P. P. Deshpande, F. Tagliaferri, S. F. Victory, S. Yan and D. C. Baker, J. Org. Chem., 60, 2964 (1995).
86. D. A. Evans, R. L. Dow, T. L. Shih, J. M. Takacs and R. Zahler, J. Am. Chem. Soc., 112, 5290 (1990).
87. M. A. Blanchette, M. S. Malamas, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, M. Kageyama and T. Tamura, J. Org. Chem., 54, 2817 (1989).
88. R. A. de Haan, M. J. Heeg and K. F. Albizati, J. Org. Chem., 58, 291 (1993).
89. G. Saha, S. S. Roy and S. Ghosh, Tetrahedron, 46, 8229 (1990).
90. I. R. Vlahov, P. I. Vlahova and R. R. Schmidt, Tetrahedron Lett., 32, 7025 (1991).
91. M. Carcano, F. Nicotra, L. Panza and G. Russo, Chem. Commun., 297 (1989).
92. L. Lay, F. Nicotra, L. Panza and A. Verani, Gazz. Chim. Ital., 122, 3458 (1992).
93. O. R. Martin and F. Xie, Carbohydr. Res., 264, 141 (1994).
94. R. Polt and T. Wijayaratne, Tetrahedron Lett., 32, 4831 (1991).
95. R. Zimmer, M. A. Grassberger, K. Baumann, G. Schulz and E. Haidl, Tetrahedron, 50, 13655 (1994).
96. M. A. Tius, A. Makriyannis, X. L. Zou and V. Abadji, Tetrahedron, 50, 2671 (1994).
97. M. A. Tius and J. Busch-Petersen, Tetrahedron, 35, 5181 (1994).
98. Y. Amate, A. García-Granados, F. A. López and A. Sáenz de Buruaga, Synthesis, 371 (1991).
99. P. Bravo, G. Resnati, F. Viani and A. Amone, J. Chem. Soc., Perkin Trans. 1, 839 (1989).
100. A. Amone, P. Bravo, M. Frigerio, G. Resnati and F. Viani, J. Chem. Res. (S), 278 (1989).
101. A. Amone, P. Bravo, G. Resnati and F. Viani, J. Chem. Soc., Perkin Trans. 1, 1315 (1991).
102. J. H. Hutchinson, E. J. McEachem, J. Scheigetz, D. Macdonald and M. Thérien, Tetrahedron Lett, 33, 4713(1992).
103. P. Kocovsky and M. Pour, J. Org. Chem., 55, 5580 (1990).
104. P. Kocovsky, V. Langer and A. Gogoll, Chem. Commun., 1026 (1990).
105. J. P. Michael and M. M. Nkwelo, Tetrahedron, 46, 2549 (1990).
106. M. L. Mihailovic, R. Vukicevic, S. Konstantinovic, S. Milosavljevic and G. Schroth, Liebigs Ann. Chem., 305 (1992).
107. H. M. C. Ferraz, C. M. R. Ribeiro, M. V. A. Grazini, T. J. Brocksom and U. Brocksom, Tetrahedron Lett, 35, 1497 (1994).
108. J. S. Baxter, M. Green and T. V. Lee, Chem. Commun., 1595 (1989).
109. J. E. Bäckvall, P. G. Andersson and J. O. Vágberg, Tetrahedron Lett., 30, 137 (1989).
110. R. C. Larock and T. R. Hightower, J. Org. Chem., 58, 5298 (1993).
111. M. Yoshikawa, E. Harada, N. Yagi, Y. Okuno, O. Muraoka, H. Aoyama and N. Murakami, Chem. Pharm. Bull. Jpn., 42, 721 (1994).
112. H. M. C. Ferraz and C. M. R. Ribeiro, Synth. Commun., 22, 399 (1992).
113. A. S. Gopalan, R. Prieto, B. Mueller and D. Peters, Tetrahedron Lett., 33, 1679 (1992).
114. G. Cardillo, M. A. Hashem and C. Tomasini, J. Chem. Soc., Perkin Trans. 1, 1487 (1990).
115. A. J. Bloodworth, R. J. Curtis and N. Mistry, Chem. Commun., 954 (1989).
116. A. J. Bloodworth, R. J. Curtis, M. D. Spencer and N. A. Tallant, Tetrahedron, 49, 2729 (1993).
117. Y. Fukuda and K. Utimoto, Synthesis, 975 (1991).
118. Y. Fukuda, S. Matsubara and K. Utimoto, J. Org. Chem., 56, 5812 (1991).
119. J. R. Hwu, J. A. Robl and B. A. Gilbert, J. Am. Chem. Soc., 114, 3125 (1992).
120. A. Arcadi, S. Cacchi and F. Marinelli, Tetrahedron Lett., 30, 2581 (1989).
121. S. Cacchi, V. Camicelli and F. Marinelli, J. Organomet. Chem., 475, 289 (1994).
122. Y. Kondo, T. Sakamoto and H. Yamanaka, Heterocycles, 29, 1013 (1989).
123. Y. Kondo, F. Shiga, N. Murata, T. Sakamoto and H. Yamanaka, Tetrahedron, 50, 11803 (1994).
124. D. E. Rudisill and J. K. Stille, J. Org. Chem., 54, 5856 (1989).
125. A. Arcadi, S. Cacchi and F. Marinelli, Tetrahedron Lett., 33, 3915 (1992).
126. A. Arcadi, S. Cacchi, V. Camicelli and F. Marinelli, Tetrahedron, 50, 437 (1994).
127. F.-T. Luo and R.-T. Wang, Tetrahedron Lett., 33, 6835 (1992).
128. M. Kimura, S. Kure, Z. Yoshida, S. Tanaka, K. Fugami and Y. Tamura, Tetrahedron Lett., 31, 4887 (1990).
129. F.-T. Luo, I. Schreuder and R.-T. Wang, J. Org. Chem., 57, 2213 (1992).
130. J. S. Swenton, D. Bradin and B. D. Gates, J. Org. Chem., 56, 6156 (1991).
131. D. Villemin and D. Goussu, Heterocycles, 29, 1255 (1989).
132. B. Seiller, C. Bruneau and P. H. Dixneuf, Chem. Commun., 493 (1994).
133. D. Bouyssi, J. Gore and G. Balme, Tetrahedron Lett., 33, 2811 (1992).
134. A. Arcadi, A. Burini, S. Cacchi, M. Delmastro, F. Marinelli and B. R. Pietroni, J. Org. Chem., 57, 976(1992).
135. V. Dalla and P. Pale, Tetrahedron Lett., 35, 3525 (1994).
136. A. Arcadi, S. Cacchi, R. C. Larock and F. Marinelli, Tetrahedron Lett., 34, 2813 (1993).
137. Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, J. Org. Chem., 56, 5816 (1991).
138. I. W. Davies, D. I. C. Scopes and T. Gallagher, Synlett, 85 (1993).
139. D. N. A Fox, D. Lathbury, M. F. Mahon, K. C. Molloy and T. Gallagher, J. Am. Chem. Soc., 113, 2652(1991).
140. D. N. A. Fox and T. Gallagher, Tetrahedron, 46, 4697 (1990).
141. D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy and T. Gallagher, Chem. Commun., 1073 (1989).
142. R. W. Shaw, D. Lathbury and T. Gallagher, Synlett, 1710 (1993).
143. T. Gallagher, I. W. Davies, S. W. Jones, D. Lathbury, M. F. Mahon, K. C. Molloy, R. W. Shaw and P. Vernon, J. Chem. Soc., Perkin Trans. 1, 433 (1992).
144. N. J. S. Huby, R. G. Kinsman, D. Lathbury, P. G. Vernon and T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 145 (1991).
145. T. Gallagher, S. W. Jones, M. F. Mahon and K. C. Molloy, J. Chem. Soc., Perkin Trans. 1, 2193 (1991).
146. D. C. Lathbury, R. W. Shaw, P. A. Bates, M. B. Hursthouse and T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 2415 (1989).
147. R. W. Shaw, D. Lathbury, M. Anderson and T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 659 (1991).
148. J. A. Marshall and X.-J. Wang, J. Org. Chem., 55, 2995 (1990).
149. R. D. Walkup, L. Guan, M. D. Mosher, S. W. Kim and Y. S. Kim, Synlett, 88 (1993).
150. R. D. Walkup and M. D. Mosher, Tetrahedron, 49, 9285 (1993).
151. J. A. Marshall and E. D. Robinson, J. Org. Chem., 55, 3450 (1990).
152. J. A. Marshall and X.-J. Wang, J. Org. Chem., 56, 960 (1991).
153. R. D. Walkup and M. D. Mosher, Tetrahedron Lett., 35, 8545 (1994).
154. R. D. Walkup and G. Park, J. Am. Chem. Soc., 112, 1597 (1990).