Chemical transformations induced by hypervalent iodine reagents

Tetrahedron

Volumn 53, Issue 4, 1997, Pages 1179-1255

  Varvoglis, Anastasios ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Hypervalent iodine; Iodanes; Iodobenzene derivatives; Iodonium compounds

Indexed keywords

ORGANOIODINE DERIVATIVE;

DECARBOXYLATION; DEGRADATION; DRUG SYNTHESIS; EPOXIDATION; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0031027260     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00970-2     Document Type: Review

References (305)

1. Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine, VCH Publishers, Inc.: New York, 1992.
2. Moriarty, R. M.; Vaid, R. K. Synthesis, 1990, 431.
3. Stang, P. J. Angew. Chem., Int. Ed. Engl., 1992, 31, 274.
4. Prakash, O.; Saini, N.; Sharma, P. K. Synlett, 1994, 221.
5. Prakash, O.; Saini, N.; Sharma, P. K. Heterocycles, 1994, 38, 409.
6. Stang, P. J. In The Chemistry of Triple-Bonded Functional Groups, Supplement C2; Patai, S., Ed.; John Wiley and Sons, Ltd.: Chichester, 1994; Vol. 2, Chapter 20, pp 1164-1182.
7. Stang, P. J. In Modern Acetylene Chemistry; Stang P. J., Diederich, F., Eds.; VCH Publishers: Weinheim, 1995; Chapter 3, pp 67-98.
8. Koser, G. F. In The Chemistry of Halides, Pseudo-Halides and Azides, Suppl. D2; Patai, S., Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995; Chapter 21, pp 1173-1274.
9. Varvoglis, A. Chimica Chronica, 1995, 24, 3.
10. Stang, P. J.; Zhdankin, V. V.; Chem. Rev., 1996, 96, 1123.
11. Varvoglis, A. Hypervalent Iodine in Organic Synthesis, Academic Press: London, in press.
12. Kita, Y.; Okuno, T.; Egi, M.; Iio, K.; Takeda, Y.; Akai, S. Synlett, 1994, 1039.
13. Okuyama, T.; Takino, T.; Sueda, T.; Ochiai, M. J. Am. Chem. Soc., 1995, 117, 3360.
14. Moriarty, R.M.; Gupta, S.C.; Hu, H.; Berenschot, D.R.; White, K.B. J. Am. Chem. Soc., 1981, 103, 686.
15. Meunier, B. Chem. Rev., 1992, 92, 1411.
16. Zefirov, N.S.; Caple, R.; Palyulin, V.A.; Berglund, B.; Tykwinski, R.; Zhdankin, V.V.; Kozmin, A.S. Izv. Akad. Nauk SSSR. Ser. Khim., 1988, 1452.
17. Ochiai, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H. Tetrahedron Lett., 1983, 24, 777.
18. Moriarty, R.M.; Hopkins, T.E.; Vaid, R.K.; Vaid, B.K.; Levy, S.G. Synlett, 1992, 847.
19. Barton, D.H.R.; Crich, D. Tetrahedron, 1985, 41, 4359.
20. Moriarty, R.M.; Vaid, R.K.; Duncan, M.P; Vaid, B.K. Tetrahedron Lett., 1987, 28, 2845.
21. Kita, Y.; Yakura, T.; Terashi, H.; Haruta, J.; Tamura, Y. Chem. Pharm. Bull., 1989, 37, 891.
22. Vasileva, V.P.; Khalfina, I.L.; Karpitskaya, L.G.; Merkushev, E.B. Zh. Org. Khim., 1987, 23, 2225.
23. Muller, P.; Godoy, J. Tetrahedron Lett., 1982, 23, 3661.
24. Barton, D.H.R.; Godfrey, C.R.A.; Morzycki, J.W.; Motherwell, W.B.; Lev, S.V. J. Chem. Soc., Perkin Trans. 1, 1982, 1947.
25. Prakash, O.; Pahuja, S.; Moriarty, R.M. Synth. Commun., 1990, 20, 1417.
26. Prakash, O.; Kumar, D.; Saini, R.K.; Singh, S.P. Synth. Commun., 1994, 24, 2167.
27. Ghosh, A.K.; McKee, S.P.; Sanders, W.M. Tetrahedron Lett., 1991, 32, 711.
28. Yan, J.; Zhong L.R.; Chen, Z.C. J. Org. Chem., 1991, 56, 459.
29. Leonard, N.J.; Bhat, B.; Wilson, S.R.; Cruikshank, K.A. J. Am. Chem. Soc., 1991, 113, 1398.
30. Moriarty, R.M.; Vaid, R.K.; Ravikumar, V.T.; Hopkins, T.E.; Farid, P. Tetrahedron, 1989, 45, 1605.
31. Rebrovic, L.; Koser, G.F. J. Org. Chem., 1984, 49, 2462.
32. Hembre, R.T.; Scott, C.P.; Norton, J.R. J. Org. Chem., 1987, 52, 3650.
33. Zhdankin, V.V.; Tykwinski, R.; Berglund, B.; Mullikin, M.; Caple, R.; Zefirov, N.S.; Kozmin, A.S. J. Org. Chem., 1989, 54, 2609.
34. Kitamura, T.; Matsuyuki, J.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1, 1991, 1607.
35. De Mico, A.; Margarita, R.; Mariani, A.; Piancatelli, G. Tetrahedron Lett., 1996, 37, 1889.
36. Moriarty, R.M.; Khosrowshahi, J.S.; Prakash, O. Tetrahedron Lett., 1985, 26, 2961.
37. Carpenter, W. J. Org. Chem., 1966, 31, 2688.
38. Zhdankin, V.V.; Mullikin, M.; Tykwinski, R.; Berglund, B.; Caple, R.; Zefirov, N.S.; Kozmin, A.S. J. Org. Chem., 1989, 54, 2605.
39. Lasne, M.C.; Thuillier, A. Compt. Rend. Acad. Sci. Paris, Ser. C, 1971, 273, 1258.
40. Moriarty, R.M.; Duncan, M.P.; Vaid, R.K.; Prakash, O. Org. Synth., 1989, 68, 175.
41. Nikas, S. Ph. D. Thesis, University of Thessaloniki, 1996.
42. Togo, H.; Aoki, M.; Yokoyama, M. Tetrahedron, 1993, 49, 8241.
43. Shah, M.; Taschner, M.J.; Koser, G.F.; Rach, N.L. Tetrahedron Lett., 1986, 27, 4557.
44. Schaumann, E.; Kirschning, A. J. Chem. Soc., Perkin Trans. 1, 1990, 1481.
45. Lee, K.; Kim, D.Y.; Oh, Y. Tetrahedron Lett., 1988, 29, 667.
46. Ochiai, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H. 1985, 33, 989.
47. Ochiai, M.; Sumi, K.; Takaoka, Y.; Kunishima, M.; Nagao, Y.; Shiro, M.; Fujita, E. Tetrahedron, 1988, 44, 4095.
48. Stang, P.J.; Ullmann, J. Ang. Chem., Int. Ed. Engl., 1991, 30, 1469.
49. Papoutsis, I.; Spyroudis, S,; Varvoglis, A. unpublished results.
50. Papoutsis, I.; Spyroudis, S.; Varvoglis, A. Tetrahedron Lett., 1996, 37, 913.
51. Ochiai, M.; Takaoka, Y.; Masaki, Y.; Inenaga, M.; Nagao, Y. Tetrahedron Lett., 1989, 30, 6701.
52. Stang, P.J.; Zhdankin, V.V. J. Am. Chem. Soc., 1991, 113, 4571.
53. Moriarty, R.M.; Epa, W.R.; Awasthi, A.K. J. Am. Chem. Soc., 1991, 113, 6315.
54. Kang, S.-K.; Lee, H.-W.; Jang, S.-B.; Kim, T.-H.; Pyun, S.-J. J. Org. Chem., 1996, 61, 2604.
55. Stang, P.J.; Blume, T.; Zhdankin, V.V. Synthesis, 1993, 35.
56. Kang, S.-K.; Lee, H.-W.; Jang, S.-B.; Ho, P.-S. J. Chem. Soc., Chem. Commun., 1996, 835.
57. Ochiai, M.; Takaoka, Y.; Sumi, K.; Nagao, Y. J. Chem. Soc., Chem. Commun., 1986, 1382.
58. Ochiai M.; Oshima, K.; Masaki, Y. Chem. Lett., 1994, 871.
59. Ochiai, M.; Kitagawa, Y.; Toyonari, M.; Uemura K. Tetrahedron Lett., 1994, 35, 9407.
60. Ochiai, M.; Uemura, K.; Masaki, Y. J. Am. Chem. Soc., 1993, 115, 2528.
61. Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc., 1991, 113, 3135.
62. Ochiai, M.; Sueda, T.; Uemura, K.; Masaki, Y. J. Org. Chem., 1995, 60, 2624.
63. Shellhamer, D.F.; Oakes, M.L. J. Org. Chem., 1978, 43, 1316.
64. Kita, Y.; Okuno, T.; Tohma, H.; Akai, S. Tetrahedron Lett., 1994, 35, 2717.
65. Tingoli, M.; Tiecco, M.; Testaferri, L.; Balducci, R. Synlett, 1993, 211.
66. Stang, P.J.; Boehshar, M.; Wingert, H.; Kitamura, T. J. Am. Chem. Soc., 1988, 110, 3272.
67. Bovonsombat, P.; McNelis, E. Tetrahedron, 1993, 49, 1525.
68. Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y. J. Am. Chem. Soc., 1991, 113, 1319.
69. Ochiai, M.; Ito, T. J. Org. Chem., 1995, 60, 2274.
70. Moriarty, R.M.; Penmasta, R.; Awasthi, A.K.: Prakash, I. J. Org. Chem., 1988, 53, 6124.
71. Williamson, B.L.; Stang, P.J.; Arif, A.M. J. Am. Chem. Soc., 1993, 115, 2590.
72. Stang, P.J.; Zhdankin, V.V. J. Am. Chem. Soc., 1991, 113, 4571.
73. Kitamura, T.; Furuki, R.; Nagata, K.; Taniguchi, H.; Stang, P.J. J. Org. Chem., 1992, 57, 6810.
74. Stang, P.J.; Kitamura, T. J. Am. Chem. Soc., 1987, 109, 7561.
75. Kitamura, T.; Tanaka, T.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1, 1991, 2892.
76. Kitamura, T.; Mihara, I.; Taniguchi, H.; Stang, P.J. J. Chem. Soc., Chem. Commun., 1990, 614.
77. Fischer, D.R.; Williamson, B.L.; Stang, P.J. Synlett, 1993, 858.
78. Liu, Z.-D.; Chen, Z.-C. Synth. Commun., 1992, 22, 1997.
79. Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc., 1991, 113, 3135.
80. Williamson, B.L.; Tykwinski, R.; Stang, P.J. J. Am. Chem. Soc., 1994, 116, 93.
81. Murch, P.; Williamson, B.L.; Stang, P.J. Synlett, 1994, 1255.
82. Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K. Fujita, E. J. Chem. Soc., Chem. Commun., 1987, 1708.
83. Lodaya, J.S.; Koser, G.F. J. Org. Chem., 1990, 55, 1513.
84. Nagaoka, T.; Sueda, T.; Ochiai, M. Tetrahedron Lett., 1995, 36, 261.
85. Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun., 1990, 118.
86. Bachi, M.D.; Bar-Ner, N.; Crittell, C.M.; Stang, P.J.; Williamson, B.L. J. Org. Chem, 1991, 56, 3912.
87. Schildknegt, K.; Bohnstedt, A.C.; Feldman, K.S.; Sambandam, A. J. Am. Chem. Soc., 1995, 117, 7544.
88. Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett., 1993, 34, 4055.
89. Tykwinski, R.; Whiteford, J.A.; Stang, P.J. J. Chem. Soc., Chem. Commun., 1993, 1800.
90. Dess, D.B.; Martin, J.C. J. Am. Chem. Soc., 1991, 113, 7277.
91. Meyer, S.D.; Schreiber, S.L. J. Org. Chem., 1994, 59, 7549.
92. Marshall, J.A.; Wang, X.-J. J. Org. Chem., 1991, 56, 960.
93. Lipshutz, B.H.; Lindsley, C.; Susfalk, R.; Gross, T. Tetrahedron Lett., 1994, 35, 8999.
94. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem., 1995, 60, 7272.
95. Corey, E.J.; Palani, A. Tetrahedron Lett., 1995, 36, 7945.
96. Boeckman, Jr., R.K.; Shair, M.D.; Vargas, J.R.; Stolz, L.A. J. Org. Chem., 1993, 58, 1295.
97. Batchelor, M.J.; Gillespie, R.J.; Golec, J.M.C.; Hedgecock, C.J.R. Tetrahedron Lett., 1993, 34, 167.
98. Ochiai, M.; Ukita, T.; Iwaki, S.; Nagao, Y.; Fujita, E. J. Org. Chem., 1989, 54, 4832.
99. Kirihara, M.; Yokoyama, S.; Kakuda, H.; Momose, T. Tetrahedron Lett., 1995, 36, 6907.
100. Moriarty, R.M.; Vaid, R.K.; Hopkins, T.E.; Vaid, B.K. Prakash, O. Tetrahedron Lett., 1990, 31, 197.
101. Schardt, B.C.; Hill, C.L. Inorg. Chem., 1983, 22, 1563.
102. Besenyi, G.; Nemeth, S.; Simandi, L.I. Tetrahedron Lett., 1993, 34, 6105.
103. Courtneidge, J.L.; Lusztyk, J.; Page, D. Tetrahedron Lett., 1994, 35, 1003.
104. De Armas, P.; Conception, J.I.; Francisco, C.G.; Hernadez, R.; Salazar, J.A.; Suarez, E. J. Chem. Soc., Perkin Trans. 1, 1989, 405.
105. De Mico, A.; Margarita, R.; Piancatelli, G. Tetrahedron Lett., 1995, 36, 3553.
106. Weiss, R.; Seubert, J. Ang. Chem., Int. Ed. Engl., 1994, 33, 891.
107. De Mico, A.; Margarita, R.; Piancatelli, G. Gazz. Chim. Ital., 1995, 125, 325.
108. Saitz, C.B.; Valderrama, J.A.; Tapia, R.; Farina, F.; Paredes, M.C. Synth. Commun., 1992, 22, 955.
109. Barret, R.; Daudon, M. Synth. Commun., 1990, 20, 1543.
110. Barret, R.; Daudon, M. Tetrahedron Lett., 1990, 31, 4871.
111. Kinugawa, M.; Masuda, Y.; Arai, H.; Nishikawa, H.; Ogasa, T.; Tomioka, S. Kasai, M. Synthesis, 1996, 633.
112. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K. Heterocycles, 1992, 33, 503.
113. McKillop, A.; McLaren, L.; Taylor, R.J.K. J. Chem. Soc., Perkin Trans. 1, 1994, 2047.
114. Pelter, A.; Elgendy, S.M.A. J. Chem. Soc., Perkin Trans. 1, 1993, 1891.
115. Karam, O.; Jacquesy, J.C.; Jouannetaud, M.P. Tetrahedron Lett., 1994, 35, 2541.
116. Neiland, O.Ya.; Kraupsha, I.L.; Gudele, I.Ya. Khim. Geterotsikl. Soedin, 1993, 12, 1653.
117. Guan, X.; Yu, Y. Youji Huaxue, 1994, 14, 80; Chem. Abstr., 1994, 121, 8817.
118. Guan, X.; Yu, Y. Youji Huaxue, 1994, 14, 80; Chem. Abstr., 1994, 121, 8817.
119. Chu, C.-S.; Lee, T.-H.; Liao, C.-C. Synlett, 1994, 635.
120. Mitchell, A.S.; Russell, R.A. Tetrahedron Lett., 1993, 34, 545.
121. Gates, B.D.; Dalidowicz, P.; Teblen, A.; Wang, S.; Swenton, J.C. J. Org. Chem., 1992, 57, 2135.
122. Murakata, M.; Yamada, K.; Hoshino, O. J. Chem. Soc., Chem. Commun., 1994, 443.
123. Callinan, A.; Chen, Y.; Morrow, G.W.; Swenton, J.C. Tetrahedron Lett., 1990, 31, 4551.
124. Kita, Y.; Takada, Y.; Ibaraki, M.; Gyuten, M.; Mihara, S.; Fujita, S.; Tohma, H. J. Org. Chem., 1996, 61, 223.
125. Prakash, O.; Tanwar, M.P.; Goyal, S.; Pahuja, S. Tetrahedron Lett., 1992, 33, 6519.
126. Spyroudis, S.; Tarantili, P. Tetrahedron, 1994, 50, 11541.
127. Papoutsis, I.; Spyroudis, S.; Varvoglis, A. Tetrahedron Lett., 1994, 35, 8449.
128. Akai, S.; Okuno, T.; Egi, M.; Takada, H.; Tohma, H.; Kita, Y. Heterocycles, 1996, 42, 47.
129. Zhdankin, V.V.; Kuehl, C.J.; Krasutsky, A.P.; Formaneck, M.S.; Bolz, J.T. Tetrahedron Lett., 1994, 35, 9677.
130. Kirschning, A.; Domann, S.; Drager, G.; Rose, L. Synlett, 1995, 767.
131. Moriarty, R.M.; Khosrowshahi, J.S. Tetrahedron Lett., 1986, 27, 2809.
132. Arimoto, M.; Yamaguchi, H.; Fujita, E.; Nagao, Y.; Ochiai, M. Chem. Pharm. Bull., 1989, 37, 3221.
133. Arimoto, M.; Yamaguchi, H.; Fujita, E.; Ochiai, M.; Nagao, Y. Tetrahedron Lett., 1987, 28, 6289.
134. Magnus, P.; Lacour, J.; Evans, P.A.; Roe, M.B.; Hulme, C. J. Am. Chem. Soc., 1996, 118, 3406.
135. Ehrenfreund, J.; Zbiral, E. Tetrahedron, 1972, 28, 1697.
136. Zbiral, E.; Nestler, G. Tetrahedron, 1970, 26, 2945.
137. Moriarty, R.M.; Khosrowshahi, J.S. Synth. Commun., 1987, 17, 89.
138. Tingoli, M.; Tiecco, M.; Chianelli, D.; Balducci, R.; Temperini, A. J. Org. Chem., 1991, 56, 6809.
139. Moriarty, R.M.; Vaid, R.K.; Ravikumar, V.T.; Vaid, B.K.; Hopkins, T.E. Tetrahedron, 1988, 44, 1603.
140. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc., 1993, 115, 9347.
141. Magnus, P.; Hulme, C. Tetrahedron Lett., 1994, 35, 8097.
142. Magnus, P.; Hulme, C.; Weber, W. J. Am. Chem. Soc., 1994, 116, 4501.
143. Kita, Y.; Tohma, H.; Mitoh, S.; Fujita, S.; Gyoten, M. Synlett, 1994, 427.
144. Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc., 1994, 116, 3684.
145. Krasutsky, A.P.; Kuehl, C.J.; Zhdankin, V.V. Synlett, 1995, 1081.
146. Tingoli, M.; Temperini, A.; Testaferri, L.; Tiecco, M. Synlett, 1995, 1129.
147. Fontana, F.; Minisci, F.; Yan, Y.M.; Zhao, L. Tetrahedron Lett., 1993, 34, 2517.
148. Prakash, O.; Rani, N.; Goyal, S. Indian J. Chem., 1992, B31, 349.
149. Prakash, O.; Saini, N. Synth. Commun., 1993, 23, 1455.
150. Patel, H.V.; Vyas, K.A.; Pandey, S.P.; Tavares, F.; Fernandes, P.S. Synth. Commun., 1991, 21, 1583.
151. Moriarty, R.M.; Vaid, R.K.; Hopkins, T.E.; Vaid, B.K.; Prakash, O. Tetrahedron Lett., 1990, 31, 201.
152. Tuncay, A.; Dustman, J.A.; Fischer, G.; Tuncay, C.I.; Suslick, K.S. Tetrahedron Lett., 1992, 33, 7647.
153. Moriarty, R.M.; Berglund, B.A.; Penmasta, R. Tetrahedron Lett., 1992, 33, 6065.
154. Moriarty, R.M.; Hu, H.; Gupta, S.C. Tetrahedron Lett., 1981, 22, 1283.
155. Moriarty, R.M.; Prakash, I.; Penmasta, R. J. Heterocyclic Chem., 1985, 22, 1581.
156. Moriarty, R.M.; Prakash, I.; Musallam. H.A. Tetrahedron Lett. ,1984, 25, 5867.
157. Turuta, A.M.; Kamernitsky, A.V.; Fadeeva, T.M.; Zhulin, A.V. Synthesis, 1985, 1129.
158. Singh, O.V. Tetrahedron Lett., 1990, 31, 3055.
159. Tamura, Y.; Shirouchi, Y.; Haruta, J. Synthesis, 1984, 231.
160. Tamura, Y.; Yakura, T.; Shirouchi, Y.; Haruta, J. Chem. Pharm. Bull., 1985, 33, 1097.
161. Singh, O.V.; Garg, C.P.; Kapoor, R.P. Synthesis, 1990, 1025.
162. Moriarty, R.M.; Khosrowshahi, J.S.; Prakash, O. Tetrahedron Lett., 1985, 26, 2961.
163. Prakash, O.; Tanwar, M.P. Bull. Chem. Soc. Jpn, 1995, 68, 1168.
164. Brunovlevskaya, I.I.; Kusainova, K.M.; Kashin, A.K. Zh. Org. Khim., 1988, 24, 358.
165. Moriarty, R.M.; Prakash, O.; Duncan, M.P. J. Chem. Soc., Perkin Trans. 1, 1987, 559.
166. Zefirov, N.S.; Samsoniya, N.S.; Kutatelatze, T.G.; Zhdankin, V.V. Zh. Org. Khim., 1991, 27, 220.
167. Cox, P.J.; Simpkins, N.S. Synlett, 1991, 321.
168. Moriarty, R.M.; Prakash, O.; Duncan, M.P.; Vaid, R.K.; Musallam. H.A. J. Org. Chem., 1987, 52, 150.
169. Moriarty, R.M.; Epa, W.R.; Penmasta, R.; Awasthi, A.K. Tetrahedron Lett., 1989, 30, 667.
170. Kim, D.Y.; Mang, J.Y.; Oh, D.Y. Synth. Commun., 1994, 24, 629.
171. Koser, G.F.; Chen, K.; Huang, Y.; Summers, C.A. J. Chem. Soc., Perkin Trans. 1, 1994, 1375.
172. Koser, G.F.; Huang, Y.; Chen, K.; Calco, K.C. J. Chem. Soc., Perkin Trans. 1, 1995, 299.
173. Moriarty, R.M.; Penmasta, R.; Awasthi, A.K.; Epa, W.R.; Prakash, I. J. Org. Chem., 1989, 54, 1101.
174. Radhakrishna, A.S.; Siraprakash, K.; Singh, B.B. Synth. Commun., 1991, 21, 1625.
175. Radhakrishna, A.S.; Augustine, B.; Siraprakash, K.; Singh, B.B. Synth. Commun., 1991, 21, 1473.
176. Moriarty, R.M.; Prakash, O.; Vavilikolanu, P.R. Synth. Commun., 1986, 16, 1247.
177. Zeng, H.; Chen, Z.C. Synth. Commun., 1993, 23, 2497.
178. Chen, D.W.; Chen, Z.C. Synthesis, 1994, 773.
179. Chen, D.W.; Chen, Z.C. Synth. Commun., 1995, 25, 1617.
180. Smith, P.A.S.; Bruckmann, E.M. J. Org. Chem., 1974, 39, 1047.
181. Barton, D.H.R.; Jaszberenyi, J.C.; Shinada, T. Tetrahedron Lett., 1993, 34, 7191.
182. Moriarty, R.M.; Hu, H. Tetrahedron Lett., 1982, 23, 1537.
183. Spyroudis, S. Ph. D. Thesis, University of Thessaloniki, 1981.
184. Couture, P.; Terlouw, J.K.; Warkentin, J. J. Am. Chem. Soc., 1996, 118, 4214.
185. Yang, R.Y.; Dai, L.X. J. Org. Chem., 1993, 58, 3381.
186. Moriarty, R.M.; Berglund, B.A.; Rao, M.S.C. Synthesis, 1993, 318.
187. Kotali, A. Tetrahedron Lett., 1994, 35, 6753.
188. Stork, G.; Zhao, K. Tetrahedron Lett., 1989, 30, 287.
189. Barton, D.H.R.; Godfrey, C.R.A.; Morzycki, J.W.; Motherwell. W.B.; Stobie, A. Tetrahedron Lett., 1982, 23, 957.
190. Motherwell, W.B.; Wilkinson, J.A. Synlett, 1991, 191.
191. Varella, E.; Varvoglis, A. Synth. Commun., 1991, 21, 531.
192. Togo, H.; Muraki, T.; Yokoyama, M. Tetrahedron Lett., 1995, 36, 7089.
193. Togo, H.; Aoki, M.; Kuramochi, T.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1, 1993, 2417.
194. Concepcion, J.I.; Francisco, C.G.; Freire, R.; Hernandez, R.; Salazar, J.A.; Suarez, E. J. Org. Chem., 1986, 51, 402.
195. Menkisoglou-Spyroudi, O.; Varvoglis, A. J. Chem. Soc., Perkin Trans. 1, 1986, 795.
196. Singh, R.; Just, G. Synth. Commun., 1988, 18, 1327.
197. Moriarty, R.M.; Khosrowshahi, J.S.; Dalecki, T.M. J. Chem. Soc., Chem. Commun., 1987, 675.
198. Graven, A.; Joergensen, K.A.; Dahl, S.; Stanczak, A. J. Org. Chem., 1994, 59, 3543.
199. Simard, M.; Su, D.; Wuest, J.D. J. Am. Chem. Soc., 1991, 113, 4696.
200. D'Auria, M.; Mauriello, G. Tetrahedron Lett., 1995, 36, 4883.
201. Boyle, R.W.; Johnson, C.K.; Dolphin, D. J. Chem. Soc., Chem. Commun., 1995, 527.
202. Moriarty, R.M.; Hu, H. Tetrahedron Lett., 1981, 22, 2747.
203. Andrews, I.P.; Lewis, N.J.; McKillop, A.; Wells, A.S. Heterocycles, 1994, 38, 713.
204. Tamura, Y.; Yakura, T.; Shirouchi, Y.; Haruta, J. Chem. Pharm. Bull., 1986, 34, 1061.
205. Koen, M.J.; Le Guyader, F.; Motherwell, W.B. J. Chem. Soc., Chem. Commun., 1995, 1241.
206. Almond, M.R.; Stimmel, J.B.; Thompson, E.A.; Loudon, G.M Org. Synth., 1987, 66, 133.
207. Verdini, A.S.; Viscomi, G.C. J. Chem. Soc., Perkin Trans. 1, 1985, 697.
208. Le, D.A.; Tatemoto, K. US 5,064,767; Chem. Abstr., 1992, 116, 129651.
209. Moriarty, R.M.; Chany, II, C.J.; Vaid, R.K.; Prakash, O.; Tuladhar, S.M. J. Org. Chem., 1993, 58, 2478.
210. Beckwith, A.L.; Dyall, L.K. Austral. J. Chem., 1990, 43, 451.
211. Moriarty, R.M.; Khosrowshahi, J.S.; Awasthi, A.K.; Penmasta, R. Synth. Commun., 1988, 18, 1179.
212. Vasudevan, A.; Koser, G.F. J. Org. Chem., 1988, 53, 5158.
213. Wasiliewski, C.; Topolski, M.; Dembkowski, L. J. Prakt. Chem., 1989, 311, 507.
214. Lazbin, I.M.; Koser, G.F.; J. Org. Chem., 1987, 52, 476.
215. Koser, G.F.; Kokil, P.B.; Shah, M. Tetrahedron Lett., 1987, 28, 5431.
216. Kikugawa, Y.; Kawase, M. Chem. Lett., 1990, 581.
217. Kikugawa, Y.; Kawase, M. J. Chem. Soc., Chem. Commun., 1991, 1354.
218. Prakash, O.; Sharma, V.; Sadana, A. J. Chem. Res. (S), 1996, 100.
219. Anderson, D.J.; Gilchrist, T.L.; Rees, C.W. J. Chem. Soc., Chem. Commun., 1971, 800.
220. Kahn, M.; Bertenshaw, S. Tetrahedron Lett., 1989, 30, 2317.
221. Ramsden, C.A.; Rose, H.L. J. Chem. Soc., Perkin Trans. 1, 1995, 615.
222. Searle, N.E.; Adams, R. J. Am. Chem. Soc., 1933, 55, 1649.
223. Hartmann, C.; Meyer, V. Ber. Deutsch. Chem. Ges., 1894, 27, 426.
224. Kitamura, T.; Nagata, K.; Nakamura, T.; Furuki, R.; Taniguchi, H. Tetrahedron, 1995, 51, 6229.
225. Kitamura, T.; Furuki, R.; Zheng, L.; Nagata, K.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H. Bull. Chem. Soc. Jpn., 1995, 68, 3637.
226. Hampton, K.G.; Harris, T.M.; Hauser, C.R. Org. Synth., 1988, Coll. 6, 928.
227. Crimmin, M.J.; Brown, A.G. Tetrahedron Lett., 1990, 31, 2017.
228. Grushin, V.V.; Demkina, I.I.; Tolstaya, T.P. J. Chem. Soc., Perkin Trans. 2, 1992, 505.
229. Chen, K.; Koser, G.F. J. Org. Chem., 1991, 55, 5764.
230. Gao, P.; Portoghese, P.S. J. Org. Chem., 1995, 60, 2276.
231. Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M. Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 2332.
232. Lubinkovski, J.J.; Arriecha, G.G.; McEwen, W.E. J. Org. Chem., 1980, 45, 2076.
233. Bumagin, N.A.; Luzikova, L.I.; Vanchikov, A.N.; Tolstaya, T.P.; Beletskaya, I.P. Izv. Akad. Nauk SSSR, Ser. Khim., 1992, 2685.
234. Bumagin, N.A.; Luzikova, L.I.; Sukhomlinova, L.I.; Tolstaya, T.P.; Beletskaya, I.P. Izv. Akad. Nauk SSSR, Ser. Khim., 1995, 394.
235. Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Jang, S.-R. Tetrahedron Lett., 1995, 36, 8047.
236. Bumagin, N.A.; Sukhomlinova, L.I.; Igushkina, S.O.; Vanchikov, A.N. Tolstaya, T.P.; Beletskaya, I.P. Izv. Akad. Nauk SSSR, Ser. Khim., 1992, 2683.
237. Bumagin, N.A.; Sukhomlinova, L.I.; Luzikova, E.V.; Tolstaya, T.P.; Beletskaya, I.P. Tetrahedron Lett., 1996, 37, 897.
238. Papoutsis, I.; Spyroudis, S.; Varvoglis, A. J. Heterocyclic Chem., in press.
239. Müller, P.; Fernandez, D. Helv. Chim. Acta, 1995, 78, 947.
240. Moriarty, R.M.; Prakash, O.; Vaid, R.K.; Zhao, L. J. Am. Chem. Soc., 1989, 111, 6443.
241. Gallos, J.K.; Koftis, T.V.; Koumbis, A. J. Chem. Soc., Perkin Trans. 1, 1994, 611.
242. Kume, M.; Kubota, T.; Iso, Y. Tetrahedron Lett., 1995, 36, 8043.
243. Yang, R.Y.; Dai, L.X.; Ma, R.J. Heteroatom. Chem., 1992, 3, 585.
244. Hadjiarapoglou, L.; Varvoglis, A. J. Heterocyclic Chem., 1988, 25, 1599.
245. Spyroudis, S.; Tarantili, P. J. Org. Chem., 1993, 58, 4885.
246. Menke, O.; Martinez, A.G.; Subramanian, L.R.; Hanack, M. Tetrahedron Lett., 1995, 36, 4055.
247. a. Saito, T.; Ayakawa, H.; Sumizawa, N.; Shizuta, T.; Motoki, S.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1, 1991, 1405.
248. b. Saito, T.; Kikuchi, H.; Kondo, A. Synthesis, 1995, 87.
249. Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett., 1975, 361.
250. Evans, D.A.; Faul, M.M.; Bilodeau, M.T. J. Am. Chem. Soc., 1994, 116, 2742.
251. Knight, J.G.; Muldowney, M.P. Synlett, 1995, 949.
252. Li, Z.; Conser, K.R.; Jacobsen, E.N. J. Am. Chem. Soc., 1993, 115, 5326.
253. Müller, P.; Baud, C.; Jacquier, Y. Tetrahedron, 1996, 52, 1543.
254. Mahy, J.P.; Bedi, G.; Battioni, P.; Mansuy, D. Tetrahedron Lett., 1988, 29, 1927.
255. Takada, H.; Nishibayashi, Y.; Ohe, K.; Uemura, S. J. Chem. Soc., Chem. Commun., 1996, 931.
256. Nishibayashi, Y.; Chiba, T.; Ohe, K.; Uemura, S. J. Chem. Soc., Chem. Commun., 1995, 1243.
257. Nishibayashi, Y.; Srivastava, S.K.; Ohe, K.; Uemura, S. Tetrahedron Lett., 1995, 36, 6725.
258. Besenyei, G.; Simandi, L.I. Tetrahedron Lett., 1993, 34, 2839.
259. Yang, R.-Y.; Dai, L.-X. Synthesis, 1993, 481.
260. Fieser, L.F.; Haddadin, M.J. Org. Synth., 1966, 46, 107.
261. Kawase, T.; Ohsawa, T.; Enomoto, T.; Oda, M. Chem. Lett., 1994, 1333.
262. Kitamura, T.; Yamane, M. J. Chem. Soc., Chem. Commun., 1995, 983.
263. Ye, X.-S.; Li, W.-K.; Wong, H.N.C. J. Am. Chem. Soc., 1996, 118, 2511.
264. Magnus, P.; Roe, M.B. Tetrahedron Lett, 1996, 37, 303.
265. Kirschning, A. J. Org. Chem., 1995, 60, 1228.
266. Lange, U.; Plitzko, W.; Blechert, S. Tetrahedron, 1995, 51, 5781.
267. Caddick, S.; Gazzard, L.; Motherwell, W.B.; Wilkinson, J.A. Tetrahedron, 1996, 52, 149.
268. Sun, L.; Li, P.; Zhao, K. Tetrahedron Lett., 1994, 35, 7147.
269. Fukase, K.; Kinoshita, I.; Kanoh, T.; Nakai, Y.; Hasuoka, A.; Kusumoto, S. Tetrahedron, 1996, 52, 3897.
270. De Armas, P.; Francisco, C.G.; Suarez, E. Ang. Chem., Int. Ed. Engl., 1992, 31, 772.
271. Francisco, C.G.; Gonzalez, C.C.; Suarez, E. Tetrahedron Lett.,; 1996, 37, 1687.
272. Francisco, C.G.; Freire, R.; Rodriguez, M.S.; Suarez, E. Tetrahedron Lett., 1995, 36, 2141.
273. De Armas, P.; Francisco, C.G.; Suarez, E. Tetrahedron Lett., 1993, 34, 7331.
274. Martin, A.; Salazar, J.A.; Suarez, E. Tetrahedron Lett., 1995, 36, 4489.
275. Moriarty, R.M.; Vaid, R.K.; Duncan, M.P.; Ochiai, M.; Inenaga, M.; Nagao, Y. Tetrahedron Lett., 1988, 29, 6913.
276. Palmisano, G.; Danieli, B.; Lesma, G.; Passarella, D. Tetrahedron, 1989, 45, 3583.
277. Cardellini, L.; Greci, L.; Maurelli, E.; Orena, M.; Tosi, G. Heterocycles, 1992, 34, 1917.
278. Zhdankin, V.V.; Kuehl, C.J.; Krasutsky, A.P.; Bolz, J.T.; Mismash, B.; Woodward, J.K.; Simonsen, A,J. Tetrahedron Lett., 1995, 36, 7975.
279. Papoutsis, I.; Spyroudis, S.; Varvoglis, A. unpublished results.
280. Kita, Y.; Takada, T.; Mihara, S.; Whelan, B.A.; Tohma, H. J. Org. Chem., 1995, 60, 7144.
281. Eberson, L.; Hartshorn, M.P.; Persson, O. Acta Chem. Scand., 1995, 49, 640.
282. Kita, Y.; Okumaka, R.; Kondo, M.; Tohma, H.; Inagaki, M.; Hatanaka, K. J. Chem. Soc., Chem. Commun., 1992, 429.
283. Kokil, P.; Patil, S.; Ravidranathan, T.; Nair, P.M. Tetrahedron Lett., 1979, 989.
284. Grieco, P.A.; Collins, J.L.; Moher, E.D.; Fleck, T.J.; Gross, R. J. Am. Chem. Soc., 1993, 115, 6078.
285. Boeckman, R.K.; Weidner, C.H.; Perni, R.B.; Nappier, J.J. J. Am. Chem. Soc., 1989, 111, 8036.
286. Ishibashi, H.; Okano, M.; Tamaki, H.; Maruyama, K.; Yakura, T.; Ikeda, M. J. Chem. Soc., Chem. Commun., 1990, 1436.
287. Moriarty, R.M.; Prakash, O.; Vavilikolanu, P.R.; Vaid, R.K.; Freeman, W.A. J. Org. Chem., 1989, 54, 4008.
288. Miki, Y.; Kobayashi, S.; Ogawa, N.; Hackiken, H. Synlett, 1994, 1001.
289. Magnus, P.; Ladlow, M.; Cairns, P.M. Tetrahedron Lett., 1987, 28, 3307.
290. Wipf, P.; Kim, Y.T.; Jahn, H. Synthesis, 1995, 1549.
291. Shair, M.D.; Yoon, T.Y.; Danishefsky, S.J. Ang. Chem., Int. Ed. Engl., 1995, 34, 1721.
292. Szantay, C.; Blasko, G.; Barczai-Beke, M.; Pechy, P.; Dornyei, G. Tetrahedron Lett., 1980, 21, 3509.
293. White, J.D.; Chong, W.K.M.; Thirring, K. J. Org. Chem., 1983, 48, 2300.
294. Schwartz, R.S.; Pham, P.T.K.; J. Org. Chem., 1988, 53, 2318.
295. Ward, R.S.; Pelter, A.; Abd-El-Ghani, A. Tetrahedron, 1996, 52, 1303.
296. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem. Soc., 1992, 114, 2175.
297. De Sousa, J.D.F.; Rodriguez, J.A.R.; Abramovitch, R.A. J. Am. Chem. Soc., 1994, 116, 9745.
298. Wipf, P.; Kim, Y. Tetrahedron Lett., 1992, 33, 5477.
299. Kishi, Y.; Nakatsuka, S.; Fukuyama, T.; Harel, M. J. Am. Chem. Soc., 1973, 95, 6493.
300. Wei-Shan, Z.; Jiang, B.; Pan, X.-F. J. Chem. Soc., Chem. Commun., 1989, 612.
301. Karunaratne, V.; Dolphin, D. J. Chem. Soc., Chem. Commun., 1995, 2105.
302. Moriarty, R.M.; Kim, J.; Guo, L. Tetrahedron Lett., 1993, 34, 4129.
303. Litkei, G.; Gulacsi, K.; Antus, S.; Blasko, G. Liebig's Ann. Chem., 1995, 1711.
304. Hernandez, R.; Velazquez, S.M.; Suarez, E.; Rodriguez, M.S. J. Org. Chem., 1994, 59, 6395.
305. Arencibia, T.; Prange, T.; Salazar, J.A.; Suarez, E. Tetrahedron Lett., 1995, 36, 6337.