Stereoselective intermolecular [2+2]-photocycloaddition reactions and their application in synthesis

Synthesis

Volumn , Issue 5, 1998, Pages 683-703

  Bach, Thorsten ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Cyclobutanes; Oxetanes; Paterno Buchi reaction; Stereoselective synthesis; 2+2 Photocycloaddition

Indexed keywords

ALKENE; CYCLOBUTANE; OXETANE DERIVATIVE;

DIASTEREOISOMER; DIMERIZATION; ISOMER; PHOTOCHEMISTRY; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0031955099     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2054     Document Type: Review

References (417)

1. Previous reviews related to this issue: De Keukeleire, D.; He, S.-L. Chem. Rev. 1993, 93, 359.
2. Inoue, Y. Chem. Rev. 1992, 92, 741.
3. Demuth, M.; Mikhail, G. Synthesis 1989, 145.
4. Schreiber, S. L. Science 1985, 227, 857.
5. Schmittel, M.; Burghart, A. Angew. Chem. 1997, 109, 2658;
6. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550.
7. Müller, F.; Mattay, J. Chem. Rev. 1993, 93, 99.
8. Mattay, J. Synthesis 1989, 233.
9. Bauld, N. L. Tetrahedron 1989, 45, 5307.
10. Mattay, J. Angew. Chem. 1987, 99, 849;
11. Angew. Chem., Int. Ed. Engl. 1987, 26, 825.
12. Mattes, S. L.; Farid, S. Y. Org. Photochem. 1983, 6, 233.
13. Wagner, P. J.; McMahon, K. J. Am. Chem. Soc. 1994, 116, 10827.
14. Hoffmann, N.; Pete, J.-P. J. Org. Chem. 1997, 62, 6952 and refs. cited therein.
15. Sakamoto, M. Chem. Eur. J. 1997, 3, 684.
16. Toda, F. Acc. Chem. Res. 1995, 28, 480.
17. Ramamurthy, V., Ed. Photochemistry in Organized and Constrained Media, VCH: Weinheim, 1991.
18. 15
19. Balzani, V.; Scandola, F. Supramolecular Photochemistry, Ellis Horwood: New York, 1991.
20. Frontiers in Supramolecular Organic Chemistry and Photochemistry, Schneider, H.-J.; Dürr, H., Eds.; VCH: Weinheim, 1990.
21. Sieburth, S. M.; Cunard, N. T. Tetrahedron 1996, 52, 6251.
22. Cornelisse, J. Chem. Rev. 1993, 93, 615.
23. Reviews: Margaretha, P. in Houben-Weyl 4th ed., Vol. E17e; de Mejiere, A., Ed.; Thieme: Stuttgart, 1997; pp 149-162.
24. Kaupp, G. in Houben-Weyl 4th ed., Vol. 5a; Müller, E., Ed.; Thieme: Stuttgart, 1975; pp 360-412.
25. Reviews: Margaretha, P. in Houben-Weyl 4th ed., Vol. E17e; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; pp 109-114.
26. Kaupp, G. in Houben-Weyl 4th ed., Vol. 5a; Müller, E., Ed.; Thieme: Stuttgart, 1975; pp 278-360.
27. Peters, K. S.; Li, B.; Lee, J. J. Am. Chem. Soc. 1993, 115, 11119 and refs. cited therein.
28. Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3.
29. For a discussion of a possible exciplex intermediate as biradical precursor, see: Caldwell, R. A.; Hrncir, D. C.; Munoz, T., Jr.; Unett, D. J. J. Am. Chem. Soc. 1996, 118, 8741 and refs. cited therein.
30. Trapping experiments: Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1991, 113, 8525.
31. Andrew, D.; Hastings, D. J.; Oldroyd, D. L.; Rudolph, A.; Weedon, A. C.; Wong, D. F.; Zhang, B. Pure Appl. Chem. 1992, 64, 1327.
32. Andrew, D.; Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870.
33. Andrew, D.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5647.
34. Reviews: Pete, J.-P. Adv. Photochem. 1996, 21, 135.
35. Mattay, J.; Conrads, R.; Hoffmann, R. in Houben-Weyl 4th ed., Vol. E21c; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; pp 3085-3132.
36. Crimmins, M. T.; Reinhold, T. L. Org. React. 1993, 44, 297.
37. Schuster, D. I. in The Chemistry of Enones; Patai, S.; Rappoport, Z., Eds.; Wiley-Interscience: New York, 1989; pp 623-756.
38. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
39. Weedon, A. C. in Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum: New York, 1984; pp 61-144.
40. Baldwin, S. W. Org. Photochem. 1981, 5, 123.
41. Bauslaugh, P. G. Synthesis 1970, 287.
42. Recent theoretical studies: Erickson, J. A.; Kahn, S. D. Tetrahedron 1993, 49, 9699.
43. Broeker, J. L.; Eksterowicz, J. E.; Belk, A. J.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 1847.
44. Froese, R. D. J.; Lange, G. L.; Goddard, J. D. J. Org. Chem. 1996, 67, 952.
45. Corey, E. J.; Bass, J. D.; le Mahieu, R.; Mitra, R. B. J. Am. Chem. Soc. 1964, 56, 5570.
46. Further selected references: Eaton, P. E. Tetrahedron Lett. 1964, 3695.
47. Challand, B. D.; de Mayo, P. J. Chem. Soc., Chem. Commun. 1968, 982.
48. Cantrell, T. S.; Haller, W. S.; Williams, J. C. J. Org. Chem. 1969, 34, 509.
49. Margaretha, P. Helv. Chim. Acta 1974, 57, 1866.
50. Mori, K.; Sasaki, M. Tetrahedron 1980, 36, 2197.
51. Berenjian, N.; de Mayo, P.; Sturgeon, M.-E.; Sydnes, L. K.; Weedon, A. C. Can. J. Chem. 1982, 60, 425.
52. Sydnes, L. K.; Stensen, W. Acta. Chem. Scand. Ser. B 1986, 40, 657.
53. Suishu, T.; Shimo, T.; Somekawa, K. Tetrahedron 1997, 53, 3545.
54. Agosta, W. C.; Lowrance, W. W., Jr. J. Org. Chem. 1970, 35, 3851.
55. Cantrell, T. S. Tetrahedron 1971, 27, 1227.
56. Swenton, J. S.; Fritzen, E. L., Jr. Tetrahedron Lett. 1979, 1951.
57. Shih, C.; Fritzen, E. L.; Swenton, J. S. J. Org. Chem. 1980, 45, 4462.
58. Quevillon, T. M.; Weedon, A. C. Tetrahedron Lett. 1996, 37, 3939.
59. Sydnes, L. K.; Hansen, K. I.; Oldroyd, D. L.; Weedon, A. C.; Jørgensen, E. Acta Chem. Scand. 1993, 47, 916.
60. Keiji, M.; Murai, O.; Hashimoto, S.; Nakamura, Y. Tetrahedron Lett. 1996, 37, 8523.
61. Determination of lifetimes of triplet 1,4-biradicals: Kaprinidis, N. A.; Lem. G.; Courtney, S. H.; Schuster, D. I. J. Am. Chem. Soc. 1993, 115, 3324.
62. Dilling, W. L.; Tabor, T. E.; Boer, F. P.; North, P. P. J. Am. Chem. Soc. 1970, 92, 1399.
63. Loutfy, R. O.; de Mayo, P. Can. J. Chem. 1972, 50, 3465.
64. Ogino, T.; Yamada, K.; Isogai, K. Tetrahedron Lett. 1977, 2445.
65. Tobe, Y.; Hoshino, T.; Kawakami, Y.; Sakai, Y.; Kimura, K.; Odaira, Y. J. Org. Chem. 1978, 43, 4334.
66. Guerry, P.; Neier, R. Chimia 1987, 41, 341.
67. Hastings, D. J.; Weedon, A. C. Can. J. Chem. 1991, 69, 1171.
68. Throughout this review the wedged lines indicate the absoute stereochemistry in enantiomers, and the bold lines (hashed or solid) the relative stereochemistry in racemic molecules, cf. Maehr, H. J. Chem. Ed. 1985, 62, 114.
69. Eaton, P. E. J. Am. Chem. Soc. 1962, 84, 2454.
70. Corey, E. J.; Nozoe, S. J. Am. Chem. Soc. 1964, 86, 1652.
71. Bowman, R. M.; Calvo, C.; McCullough, J. J.; Rasmussen, P. W.; Snyder, F. F. J. Org. Chem. 1972, 37, 2084.
72. Tada, M.; Kokubo, T.; Sato, T. Tetrahedron 1972, 28, 2121.
73. Margaretha, P. Chimia 1975, 29, 203.
74. Tada, M.; Nieda, Y. Bull. Chem. Soc. Jpn. 1988, 61, 1416.
75. Lange, G. L.; Decicco, C. P.; Willson, J.; Strickland, L. A. J. Org. Chem. 1989, 54, 1805.
76. Hatsui, T.; Kitashima, T.; Takeshita, H. Bull. Chem. Soc. Jpn. 1994, 67, 293.
77. Buback, M.; Buenger, J.; Tietze, L. F. Chem. Ber. 1992, 125, 2577.
78. Lewis, F. D.; Reddy, G. D.; Elbert, J. E.; Tillberg, B. E.; Meltzer, J. A.; Kojima, M. J. Org. Chem. 1991, 56, 5311.
79. Termont, D.; De Keukeleire, D.; Vandewalle, M. J. Chem. Soc., Perkin Trans. 1 1977, 2349.
80. Bonvalet, C.; Souquant, J.; Feigenbaum, A.; Pete, J.-P.; Scholler, D. Bull. Soc. Chim. Fr. 1994, 131, 687.
81. Griesbeck, A. G.; Stadtmüller, S.; Busse, H.; Bringmann, G.; Buddrus, J. Chem. Ber. 1992, 125, 933.
82. El-Nabi, H. A. A. Tetrahedron 1997, 53, 1813.
83. Bourgin, D.; Büchel, R.; Gerber, P.; Keese, R. Tetrahedron Lett. 1994, 35, 3267.
84. Sano, T.; Toda, J.; Horiguchi, Y.; Imafuku, K.; Tsuda, Y. Heterocycles 1981, 16, 1463.
85. For recent work, see Sano, T.; Koseki, N.; Saitoh, T.; Horiguchi, Y.; Toda, J.; Kiuchi, F.; Tsuda, Y. Chem. Pharm. Bull. 1997, 45, 608 and refs. therein.
86. Demuth, M.; Pandey, B.; Wietfeld, B.; Said, H.; Viader, J. Helv. Chim. Acta 1988, 71, 1392.
87. Griesbeck, A. G.; Mauder, H., Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70.
88. Somekawa, K.; Hara, R.; Kinnami, K.; Muraoka, F.; Suishu, T.; Shimo, T. Chem. Lett. 1995, 407.
89. Sano, T.; Horiguchi, Y.; Tsuda, Y. Chem. Pharm. Bull. 1987, 35, 23.
90. Sugihara, Y.; Morokoshi, N.; Murata, I. Tetrahedron Lett. 1977, 18, 3887.
91. Ziegler, F. E.; Ried, G. R.; Studt, W. L.; Wender, P. A. J. Org. Chem. 1977, 42, 1991.
92. Cargill, R. L.; Morton, G. H.; Bordner, J. J. Org. Chem. 1980, 45, 3929.
93. Schreiber, S. L.; Santini, C. J. Am. Chem. Soc. 1984, 106, 4038.
94. Kosugi, H.; Sekiguchi, S.; Sekita, R.-i.; Uda, H. Bull. Chem. Soc. Jpn. 1976, 49, 520.
95. Tomioka, K.; Tanaka, M.; Koga, K. Tetrahedron Lett. 1982, 23, 3401.
96. Tomioka, K.; Tanaka, M.; Koga, K. Chem. Pharm. Bull. 1989, 37, 1201.
97. Alibés, R.; Bourdelande, J. L.; Font, J. Tetrahedron: Asymmetry 1991, 2, 1391.
98. Alibés, R.; Bourdelande, J. L.; Font, J. Tetrahedron Lett. 1993, 34, 7455.
99. Alibés, R.; Bourdelande, J. L.; Font, J.; Gregori, A.; Parella, T. Tetrahedron 1996, 52, 1267.
100. Alibés, R.; Bourdelande, J. L.; Font, J.; Parella, T. Tetrahedron 1996, 52, 1279.
101. Hoffmann, N.; Buschmann, H.; Raabe, G.; Scharf, H.-D. Tetrahedron 1994, 50, 11167.
102. Wiesner, K. Tetrahedron 1975, 31, 1655.
103. Marini-Bettolo, G.; Sahoo, S. P.; Poulton, G. A.; Tsai, T. Y. R.; Wiesner, K. Tetrahedron 1980, 36, 719.
104. Singh, P. J. Org. Chem. 1971, 36, 3334.
105. Lange, G. L.; Lee, M. Synthesis 1986, 117.
106. Lange, G. L., McCarthy, F. C. Tetrahedron Lett. 1978, 4749.
107. Williams, J. R.; Callahan, J. F. J. Org. Chem. 1980, 45, 4479.
108. Williams, J. R.; Callahan, J. F.; Lin, C. J. Org. Chem. 1983, 48, 3162.
109. van Audenhove, M.; de Keukeleire, D.; Vandewalle, M. Tetrahedron Lett. 1980, 21, 1979.
110. van Hijfte, L.; Vandewalle, M. Tetrahedron 1984, 40, 4371.
111. Furan-3(2H)-ones: Baldwin, S. W.; Mazzuckelli, T. J. Tetrahedron Lett. 1986, 27, 5975.
112. Liu, H.-J.; Chan, W. H. Can. J. Chem. 1982, 60, 1081.
113. Seebach, D.; Zimmermann, J. Helv. Chim. Acta 1986, 69, 1147.
114. Sato, M.; Abe, Y.; Kaneko, C. J. Chem. Soc., Perkin Trans. 1 1990, 1779.
115. Lange, G. L.; Organ, M. G. Tetrahedron Lett. 1993, 34, 1425.
116. Iwata, C.; Takemoto, Y.; Doi, M.; Imanishi, T. J. Org. Chem. 1988, 53, 1623.
117. Fetizon, M.; Khac, D. D.; Tho, N. D. Tetrahedron Lett. 1986, 27, 1777.
118. Benchikh-le-Hocine, M.; Khac, D. D.; Cervantes, H.; Fetizon, M. New J. Chem. 1986, 10, 715.
119. Paquette, L. A.; Lin, H. S.; Gunn, B. P.; Coghlan, M. J. J. Am. Chem. Soc. 1988, 110, 5818.
120. Paquette, L. A.; Moriarty, K. J.; Shen, C.-C. Isr. J. Chem. 1991, 31, 195.
121. Strunz, G. M.; Bethell, R.; Dumas, M. T.; Boyonoski, N. Can. J. Chem. 1997, 75, 742.
122. Moëns, L.; Baizer, M. M.; Little, R. D. J. Org. Chem. 1986, 51, 4497.
123. Ziegler, F. E.; Kloek, J. A. Tetrahedron 1977, 33, 373.
124. Exon, C; Nobbs, M.; Magnus, P. Tetrahedron 1981, 37, 4515.
125. For an illustrative example, see Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimizu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc. 1989, 111, 3707.
126. Neh, H.; Blechert, S.; Schnick, W.; Jansen, M. Angew. Chem. 1984, 96, 903;
127. Angew. Chem., Int. Ed. Engl. 1984, 23, 905.
128. Berkowitz, W. F.; Perumattam, J.; Amarasekara, A. Tetrahedron Lett. 1985, 26, 3665.
129. Cervantes, H.; Khac, D. D.; Fetizon, M.; Guir, F.; Beloeil, J.-C.; Lallemand, J.-Y.; Prange, T. Tetrahedron 1986, 42, 3491.
130. Benchikh-le-Hocine, M.; Khac, D. D.; Fetizon, M.; Hanna, I.; Zeghdoudi, R. Synth. Commun. 1987, 17, 913.
131. Neh, H.; Kühling, A.; Blechert, S. Helv. Chim. Acta 1989, 72, 101.
132. Blechert, S.; Kleine-Klausing, A. Angew. Chem. 1991, 103, 428;
133. Angew. Chem., Int. Ed. Engl. 1991, 30, 412.
134. Blechert, S.; Jansen, R.; Velder, J. Tetrahedron 1994, 50, 9649.
135. Blechert, S.; Müller, R.; Beitzel, M. Tetrahedron 1992, 48, 6953.
136. Tolbert, L. M.; Ali, M. B. J. Am. Chem. Soc. 1982, 104, 1742.
137. Lange, G. L.; Decicco, C.; Tan, S. L.; Chamberlain, G. Tetrahedron Lett. 1985, 26, 4707.
138. Lange, G. L.; Decicco, C.; Lee, M. Tetrahedron Lett. 1987, 28, 2833.
139. Herzog, H.; Koch, H.; Scharf, H.-D.; Runsink, J. Tetrahedron 1986, 42, 3547.
140. Herzog, H.; Koch, H.; Scharf, H.-D.; Runsink, J. Chem. Ber. 1987, 120, 1737.
141. Hoffmann, N.; Scharf, H.-D.; Runsink, J. Tetrahedron Lett. 1989, 30, 2637.
142. Hoffmann, N.; Scharf, H.-D. Liebigs Ann. Chem. 1991, 1273.
143. Curtius, F. W.; Scharf, H.-D. Tetrahedron: Asymmetry 1996, 7, 2957.
144. Meyers, A. I.; Fleming, S. A. J. Am. Chem. Soc. 1986, 108, 306.
145. Demuth, M.; Palomer, A.; Sluma, H.-D.; Dey, A. K.; Krüger, C.; Tsay, Y.-H. Angew. Chem. 1986, 98, 1093;
146. Angew. Chem., Int. Ed. Engl. 1986, 25, 1117.
147. Sato, M.; Takayama, K.; Furuya, T.; Inukai, N.; Kaneko, C. Chem. Pharm. Bull. 1987, 35, 3971.
148. Sato, M.; Murakami, M.; Kaneko, C.; Furuya, T. Tetrahedron 1993, 49, 8529.
149. Organ, M. G.; Froese, R. D. J.; Goddard, J. D.; Taylor, N. J.; Lange, G. L. J. Am. Chem. Soc. 1994, 116, 3312.
150. Seebach, D.; Zimmermann, J.; Gysel, U.; Ziegler, R.; Ha, T.-K. J. Am. Chem. Soc. 1988, 110, 4763.
151. Lange, G. L.; Organ, M. G.; Roche, M. R. J. Org. Chem. 1992, 57, 6000.
152. Kaneko, C.; Sato, M.; Sakaki, J.; Abe, Y. J. Heterocycl. Chem. 1990, 27, 25.
153. White, J. D.; Gupta, D. N. J. Am. Chem. Soc. 1966, 88, 5364.
154. White, J. D.; Gupta, D. N. J. Am. Chem. Soc. 1968, 90, 6171.
155. Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. J. Am. Chem. Soc. 1973, 95, 532.
156. Lange, G. L.; Neidert, E. E.; Orrom, W. J.; Wallace, D. J. Can. J. Chem. 1978, 56, 1628.
157. Baldwin, S. W.; Crimmins, M. T. J. Am. Chem. Soc. 1980, 102, 1198.
158. Baldwin, S. W.; Crimmins, M. T. J. Am. Chem. Soc. 1982, 104, 1132.
159. Tietze, L.-F.; Glüsenkamp, K.-H.; Nakane, M.; Hutchinson, C. R. Angew. Chem. 1982, 94, 81;
160. Angew. Chem., Int. Ed. Engl. 1982, 21, 70.
161. Choudhuri, R. K.; Ikeda, T.; Hutchinson, C. R. J. Am. Chem. Soc. 1984, 106, 6004.
162. Baldwin, S. W.; Fredericks, J. E. Tetrahedron Lett. 1982, 23, 1235.
163. Sato, M.; Sekiguchi, K.; Kaneko, C. Chem. Lett. 1985, 1057.
164. Sato, M.; Takayama, K.; Abe, Y.; Furuya, T.; Inukai, N.; Kaneko, C. Chem. Pharm. Bull. 1990, 38, 336.
165. Hansson, T.; Wickberg, B. J. Org. Chem. 1992, 57, 5370.
166. Hatsui, T.; Wang, J.-J.; Ikeda, S.-y.; Takeshita, H. Synlett 1995, 35.
167. Hatsui, T.; Wang, J.-J.; Takeshita, H. Bull. Chem. Soc. Jpn. 1995, 68, 2393.
168. Smith, A. B., III; Sulikowski, G. A.; Fujimoto, K. J. Am. Chem. Soc. 1989, 111, 8039.
169. Smith, A. B., III; Sulikowski, G. A.; Sulikowski, M. M:; Fujimoto, K. J. Am. Chem. Soc. 1992, 114, 2567.
170. Sulikowski, M. M.; Davies, G. E. R. E.; Smith, A. B., III J. Chem. Soc. Perkin Trans. 1 1992, 979.
171. Salomon, R. G.; Sachinvala, N. D.; Raychaudhuri, S. R.; Miller, D. B. J. Am. Chem. Soc. 1984, 106, 2211.
172. Salomon, R. G.; Sachinvala, N. D.; Roy, S.; Basu, B.; Raychaudhuri, S. R.; Miller, D. B.; Sharma, R. B. J. Am. Chem. Soc., 1991, 115, 3085.
173. Salomon, R. G.; Basu, B.; Roy, S.; Sachinvala, N. D. J. Am. Chem. Soc. 1991, 115, 3096.
174. Hara, M.; Odaira, Y.; Tsutsumi, S. Tetrahedron 1966, 22, 95.
175. Hatsui, T.; Ikeda, S.-y., Takeshita, H. Bull. Chem. Soc. Jpn. 1993, 66, 870.
176. Lange, G. L.; Lee, M. Tetrahedron Lett. 1985, 26, 6163.
177. Haga, N.; Ishikawa, I.; Takayanagi, H.; Ogura, H. Bull. Chem. Soc. Jpn. 1994, 67, 728.
178. Bruneel, K.; De Keukeleire, D.; Vandewalle, M. J. Chem. Soc., Perkin Trans. 1 1984, 1697.
179. Lange, G. L.; Decicco, C. P. Tetrahedron Lett. 1988, 29, 2613.
180. Corey, E. J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. 1964, 86, 485.
181. For approaches via an intramolecular photocycloaddition, see: Heathcock, C. H.; Badger, R. A. J. Chem. Soc., Chem. Commun. 1968, 1510.
182. Yoshihara, K.; Ohta, Y.; Sakai, T.; Hirose, Y. Tetrahedron Lett. 1969, 2263.
183. Wiesner, K.; Poon, L.; Jirkovsky, L.; Fishman, M. Can. J. Chem. 1969, 47, 433.
184. Zurflüh, R.; Dunham, L. L.; Spain, V. L.; Siddall, J. B. J. Am. Chem. Soc. 1970, 92, 425.
185. Tumlinson, J. H.; Gueldner, R. C.; Hardee, D. D.; Thompson, A. C.; Hedin, P. A.; Minyard, J. P. J. Org. Chem. 1971, 36, 2616.
186. Rosini, G.; Marotta, E.; Raimondi, A.; Righi, P. Tetrahedron Asymmetry 1991, 2, 123.
187. Langer, K.; Mattay, J. J. Org. Chem. 1995, 60, 7256.
188. For references, see: Quinkert, G. Synform 1987, 5, 125.
189. Mori, K.; Nagano, E. Liebigs Ann. 1991, 341.
190. Miyano, K.; Ohfune, Y.; Azuma, S.; Matsumoto, T. Tetrahedron Lett. 1974, 1545.
191. For a related approach: Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635.
192. Tanaka, M.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1985, 26, 3035.
193. Tanaka, M.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1985, 26, 6109.
194. Tanaka, M.; Tomioka, K.; Koga, K. Tetrahedron 1994, 50, 12829.
195. Tanaka, M.; Tomioka, K.; Koga, K. Tetrahedron 1994, 50, 12843.
196. See also: Sato, M.; Ohuchi, H.; Abe, Y.; Kaneko, C. Tetrahedron Asymmetry 1992, 3, 313.
197. Somekawa, K.; Hara, R.; Kinnami, K.; Muraoka, F.; Suishu, T.; Shimo, T. Chem. Lett. 1995, 407.
198. Reviews: Wong, H. N. C.; Lau, K.-L.; Tam, K.-F. Top. Curr. Chem. 1986, 133, 85.
199. Wong, H. N. C., Fitjer, L.; Heuschmann, M.; Mann, G.; Muchall, H. M. in Houben-Weyl 4th ed., Vol. E17e; de Mejiere, A., Ed.; Thieme: Stuttgart, 1997; pp 435-610.
200. Reviews: de Mayo, P. Acc. Chem. Res. 1971, 4, 41.
201. Oppolzer, W. Acc. Chem. Res. 1982, 15, 135.
202. Buchi, G.; Carlson, J. A.; Powell, J. E., Jr.; Tietze, L.-F. J. Am. Chem. Soc. 1970, 92, 2165.
203. Büchi, G.; Carlson, J. A.; Powell, J. E., Jr.; Tietze, L.-F. J. Am. Chem. Soc. 1973, 95, 540.
204. 80,83,84
205. Baldwin, S. W.; Wilkinson, J. M. J. Am. Chem. Soc. 1980, 102, 3634.
206. Sato, M.; Ogasawara, H.; Sekiguchi, K.; Kaneko, C. Heterocycles 1984, 22, 2563.
207. Baldwin, S. W.; Martin, G. F., Jr.; Nunn, D. S. J. Org. Chem. 1985, 50, 5720.
208. Sato, M.; Takayama, K.; Sekiguchi, K.; Abe, Y.; Furuya, T.; Inukai, N.; Kaneko, C. Chem. Lett. 1989, 1925.
209. Sato, M.; Abe, Y.; Takayama, K.; Sekiguchi, K.; Kaneko, C.; Inoue, N.; Furuya, T.; Inukai, N. J. Heterocycl. Chem. 1991, 25, 241.
210. Sato, M.; Sunami, S.; Kogawa, T.; Kaneko, C. Chem. Lett. 1994, 2191.
211. Review on eight-membered ring synthesis: Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
212. Grayon, D. H.; Wilson, J. R. H. J. Chem. Soc., Chem. Comun. 1984, 1695.
213. Disanayaka, B. W.; Weedon, A. C. J. Chem. Soc., Chem. Comun. 1985, 1282.
214. Challand, B. D.; Hikino, H.; Komis, G.; Lange, G.; de Mayo, P. J. Org. Chem. 1969, 34, 794.
215. Tietze, L.-F.; Reichert, U. Angew. Chem. 1980, 92, 832;
216. Angew. Chem., Int. Ed. Engl. 1980, 19, 830.
217. Liu, H.-J.; Lee, S. P. Tetrahedron Lett. 1977, 3699.
218. For a detailed review on intramolecular [2+2]-photocycloaddition reactions followed by this type of cleavage: Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003.
219. Booker-Milburn, K. I.; Cowell, J. K.; Harris, L. J. Tetrahedron Lett. 1994, 35, 3883.
220. Wender, P. A.; Lechleiter, J. C. J. Am. Chem. Soc. 1978, 100, 4321.
221. Lange, G. L.; Gottardo, C. J. Org. Chem. 1995, 60, 2183.
222. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921.
223. Lange, G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 6607.
224. Guthrie, R. W.; Philipp, A.; Valenta, Z.; Wiesner, K. Tetrahedron Lett. 1965, 2945.
225. Guthrie, R. W.; Valenta, Z.; Wiesner, K. Tetrahedron Lett. 1966, 4645.
226. Wiesner, K.; Uyeo, S.; Philipp, A.; Valenta, Z. Tetrahedron Lett. 1968, 6279.
227. Wiesner, K.; Ho, P.-T.; Chang, D.; Lam, Y. K.; Pan, C. S. J.; Ren, W. Y. Can. J. Chem. 1973, 51, 3978.
228. Hollis, W. G., Jr.; Lappenbusch, W. C.; Everberg, K. A.; Woleben, C. M. Tetrahedron Lett. 1993, 34, 7517.
229. Bagli, J. F.; Bogri, T. Tetrahedron Lett. 1969, 1639.
230. Manh, D. D. K.; Ecoto, J.; Fetizon, M.; Colin, H.; Diez-Masa, J.-C. J. Chem. Soc., Chem. Commun. 1981, 953.
231. Nagaoka, H.; Miyaoka, H.; Yamada, Y. Tetrahedron Lett. 1990, 31, 1573.
232. Termont, D.; De Clercq, P.; De Keukeleire, D.; Vandewalle, M. Synthesis 1977, 46.
233. Van Audenhove, M.; De Keukeleire, D.; Vandewalle, M. Bull. Soc. Chim. Belg. 1981, 90, 255.
234. Van Hijfte, L.; Vandewalle, M. Tetrahedron Lett. 1982, 23, 2229.
235. Review on sesquiterpene synthesis: Vandewalle, M.; De Clercq, P. Tetrahedron 1985, 41, 1767.
236. De Clercq, P.; Vandewalle, M. J. Org. Chem. 1977, 42, 3447.
237. Kok, P.; De Clercq, P. J.; Vandewalle, M. E. J. Org. Chem. 1979, 44, 4553.
238. Demuynck, M.; De Clercq, P. J.; Vandewalle, M. J. Org. Chem. 1979, 44, 4863.
239. Devreese, A. A.; De Clercq, P. J.; Vandewalle, M. Tetrahedron Lett. 1980, 21, 4767.
240. Devreese, A. A.; Demuynck, M.; De Clercq, P. J.; Vandewalle, M. Tetrahedron 1983, 39, 3039.
241. Devreese, A. A.; Demuynck, M.; De Clercq, P. J.; Vandewalle, M. Tetrahedron 1983, 39, 3049.
242. Suginome, H.; Nakayama, Y. Tetrahedron 1994, 50, 7771.
243. Williams, J. R.; Lin, C.; Chodosh, D. F. J. Org. Chem. 1985, 50, 5815.
244. Liu, H. J.; Valenta, Z.; Wilson, J. S.; Yu, T. T. J. Can. J. Chem. 1969, 47, 509.
245. Lange, G. L.; Huggins, M.-A.; Neidert, E. Tetrahedron Lett. 1976, 4409.
246. Wender, P. A.; Lechleiter, J. C. J. Am. Chem. Soc. 1977, 99 ,267.
247. Wender, P. A.; Hubbs, J. C. J. Org. Chem. 1980, 45, 365.
248. Wender, P. A.; Letendre, L. J. J. Org. Chem. 1980, 45, 367.
249. Williams, J. R.; Callahan, J. F. J. Chem. Soc., Chem. Commun. 1979, 404.
250. Williams, J. R.; Callahan, J. F. J. Chem. Soc., Chem. Commun. 1979, 405.
251. Williams, J. R.; Callahan, J. F. J. Org. Chem. 1980, 45, 4475.
252. Williams, J. R.; Cleary, T. P. J. Chem. Soc., Chem. Commun. 1982, 626.
253. Wender, P. A.; Eck, S. L. Tetrahedron Lett. 1982, 23, 1871.
254. Audenaert, F.; De Keukeleire, D.; Vandewalle, M. Tetrahedron 1987, 43, 5593.
255. Wilson, S. R.; Phillips, L. R.; Pelister, Y.; Huffman, J. C. J. Am. Chem. Soc. 1979, 101, 7373.
256. Lange, G. L.; So, S.; Lautens, M.; Lohr, K. Tetrahedron Lett. 1981, 22, 311.
257. Wender, P. A.; Lechleiter, J. C. J. Am. Chem. Soc. 1980, 102, 6340.
258. Cargill, R. L.; Jackson, T. E.; Peet, N. P.; Pond, D. M. Acc. Chem. Res. 1974, 7, 106.
259. Shimo, T.; Ohshima, K.; Somekawa, K.; Kawaminami, M. Bull. Chem. Soc. Jpn. 1994, 67, 2891.
260. Liu, H. J.; Kulkarni, M. G. Tetrahedron Lett. 1985, 26, 4847.
261. Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116.
262. Smith, A. B., III; Jerris, P. J. J. Am. Chem. Soc. 1981, 103, 194.
263. Lange, G. L.; Decicco, C. P.; Willson, J.; Strickland, L. A. J. Org. Chem. 1989, 54, 1805.
264. Corey, E. J.; Liu, K. Tetrahedron Lett. 1997, 38, 7491.
265. Sano, T.; Toda, J.; Ohshima, T.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40, 873.
266. Ue, M.; Ohnishi, Y.; Kobiro, K.; Kakiuchi, K.; Tobe, Y.; Odaira, Y. Chem. Lett. 1990, 149.
267. Nath, A.; Ghosh, A.; Venkateswaran, R. V. J. Org. Chem. 1992, 57, 1467.
268. Kobayashi, K.; Suzuki, M.; Suginome, H. J. Org. Chem. 1992, 57, 599.
269. Paternò, E.; Chieffi, G. Gazz. Chirn. Ital. 1909, 39-1, 341.
270. Buchi, G.; Inman, C. G.; Lipinsky, E. S. J. Am. Chem. Soc. 1954, 76, 4327.
271. Reviews: Mattay, J.; Conrads, R.; Hoffmann, R. in Houben-Weyl 4th ed., Vol. E21c; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; pp. 3133-3178.
272. Porco, J. A.; Schreiber, S. L. in Comprehensive Organic Synthesis, Vol. 5; Trost, B., Ed.; Pergamon Press: Oxford, 1991; pp 151-192.
273. Carless, H. A. J. in Synthetic Organic Photochemistry, Horspool, W. M., Ed.; Plenum Press: New York, 1984; pp 425-487.
274. Jones, G., II in Organic Photochemistry, Vol. 5; Padwa, A., Ed.; Dekker: New York, 1981; pp 1-123.
275. Arnold, D. R. Adv. Photochem. 1968, 6, 301.
276. Review: Bach, T. Liebigs Ann./Recueil 1997, 1627.
277. Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1981, 103, 6255.
278. Caldwell, R. A.; Majima, T.; Pac, C. J. Am. Chem. Soc. 1982, 104, 629.
279. Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819.
280. Wilson, R. M.; Wunderly, S. W.; Walsh, T. F.; Musser, A. K.; Outcalt, R.; Geiser, F.; Gee, S. K.; Brabender, W.; Yerino, L., Jr.; Conrad, T. T.; Tharp, G. A. J. Am. Chem. Soc. 1982, 104, 4429.
281. Adam, W.; Kliem, U.; Lucchini, V. Tetrahedron Lett. 1986, 27, 2953.
282. Adam, W.; Kliem, U.; Mosandl, T.; Peters, E.-M.; Peters, K.; von Schnering, H. G. J. Org. Chem. 1988, 55, 4986.
283. Adam, W.; Kliem, U.; Lucchini, V. Liebigs Ann. 1988, 869.
284. Schnapp, K. A.; Wilson, R. M.; Ho, D. M. J. Am. Chem. Soc. 1990, 112, 3700 and refs. cited therein.
285. Mattay, J.; Gersdorf, J.; Leismann, H.; Steenken, S. Angew. Chem. 1984, 96, 240-241;
286. Angew. Chem., Int. Ed. Engl. 1984, 23, 249.
287. Gersdorf, J.; Mattay, J.; Gömer, H. J. Am. Chem. Soc. 1987, 109, 1203.
288. Mattay, J.; Gersdorf, J.; Buchkremer, K. Chem. Ber. 1987, 120, 307.
289. Arnold, D. R.; Hinman, R. L.; Glick, A. H. Tetrahedron Lett. 1964, 1425.
290. Caldwell, R. A.; Sovocool, G. W.; Gajewski, R. P. J. Am. Chem. Soc. 1973, 95, 2549.
291. Schroeter, S. H.; Orlando, C. M., Jr. J. Org. Chem. 1969, 34, 1181.
292. Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Chem. Commun. 1987, 964.
293. Khan, N.; Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Perkin Trans. 1 1991, 865.
294. Some examples: Ryang, H.-S.; Shima, K.; Sakurai, H. J. Am. Chem. Soc. 1971, 93, 5270.
295. Ruotsalainen, H. Acta Chem. Scand., Ser B 1978, B32, 417.
296. Kato, T.; Sato, M.; Kitagawa, Y. Chem. Pharm. Bull. 1975, 23, 365.
297. Shimizu, N.; Yamaoka, S.; Tsuno, Y. Bull. Chem, Soc. Jpn. 1983, 56, 3853.
298. Barltrop, J. A.; Carless, H. A. J. J. Am. Chem. Soc. 1972, 94, 1951.
299. Turro, N. J.; Wriede, P. A. J. Am. Chem. Soc. 1970, 92, 320-329.
300. Yang, N. C.; Eisenhardt, W. J. Am. Chem. Soc. 1971, 93, 1277.
301. Funke, C. W.; Cerfontain, H. J. Chem. Soc., Perkin Trans. 2 1976, 1902.
302. Yang, N. C.; Kimura, M.; Eisenhardt, W. J. Am. Chem. Soc. 1973, 95, 5058.
303. Carless, H. A. J. Tetrahedron Lett. 1973, 3173.
304. Carless, H. A. J. J. Chem. Soc., Perkin Trans. 2 1974, 834.
305. Cyclopentene: Gold, E. H.; Ginsburg, D. Angew. Chem. 1966, 78, 207;
306. Angew. Chem., Int. Ed. Engl. 1966, 5, 246.
307. Cyclohexene: Bradshaw, J. S. J. Org. Chem. 1966, 31, 237.
308. Maleic acid anhydride: Turro, N. J.; Wriede, P. A.; Dalton, J. C.; Arnold, D.; Glick, A. H. J. Am. Chem. Soc. 1967, 89, 3950.
309. 1,3-Dioxol-2-one: Araki, Y.; Nagasawa, J.-i.; Ishido, Y. J. Chem. Soc., Perkin Trans. 1 1981, 12.
310. 2,2-Dimethyl-1,3-dioxole: Scharf, H.-D.; Mattay, J. Tetrahedron Lett. 1976, 3509.
311. 4-Oxazolin-2-one: Scholz; K.-H.; Heine, H.-G.; Hartmann, W. Tetrahedron Lett. 1978, 1467.
312. 2,3-Dihydro-2,2-dimethyloxazole: Weuthen, M.; Scharf, H.-D.; Runsink, J. Chem. Ber. 1987, 120, 1023.
313. Shima, K.; Sakai, Y.; Sakurai, H. Bull. Chem. Soc. Jpn. 1971, 44, 215.
314. Jones, G., II; Khalil, Z. H.; Phan, X. T.; Chen, T.-J.; Welankiwar, S. Tetrahedron Lett. 1981, 22, 3823.
315. Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Plath, M. W.; Runsink, J. J. Am. Chem. Soc. 1989, 111, 5367.
316. Griesbeck, A. G.; Stadtmüller, S. J. Am. Chem. Soc. 1990, 112, 1281.
317. Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457.
318. Carless, H. A. J.; Haywood, D. J. J. Chem. Soc., Chem. Commun. 1980, 1067.
319. Griesbeck, A. G.; Stadtmüller, S. Chem. Ber. 1990, 123, 357.
320. Griesbeck, A. G.; Stadtmüller, S. J. Am. Chem. Soc. 1991, 113, 6923.
321. Griesbeck, A. G.; Mauder, H.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Chem. Ber. 1991, 124, 407.
322. Buhr, S.; Griesbeck, A. G.; Lex, J.; Mattay, J.; Schröer, J. Tetrahedron Lett. 1996, 37, 1195.
323. Ruotsalainen, H.; Kärki, T. Acta Chem. Scand., Ser B 1983, B37, 151.
324. Araki, Y.; Nagasawa, J.-i.; Ishido, Y. Carbohydr. Res. 1981, 97, 77.
325. Kather, K. Ph. D. Thesis, University of Münster, Münster 1996.
326. Bach, T. Angew. Chem. 1996, 108, 976;
327. Angew. Chem., Int. Ed. Engl. 1996, 35, 884.
328. Bach, T., Schröder, J. manuscript in preparation.
329. Döpp, D.; Memarian, H. R.; Fischer, M. A.; van Eijk, A. M. J.;Varma, C. A. G. O. Chem. Ber. 1992, 125, 983.
330. Döpp, D.; Fischer, M.-A. Recl. Trav. Chim. Pays-Bas 1995, 114, 498.
331. Kubota, T.; Shima, K.; Toki, S.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1969, 1462.
332. Shima, K.; Kubota, T.; Sakurai, H. Bull. Chem. Soc. Jpn. 1976, 49, 2567.
333. Carless, H. A. J.; Maitra, A. K. Tetrahedron Lett. 1977, 1411.
334. Fleming, S.; Gao, J. J. Tetrahedron Lett. 1997, 38, 5407.
335. see also: Sakurai, H.; Shima, K.; Aono, I. Bull. Chem. Soc. Jpn. 1965, 38, 1227.
336. Carless, H. A. J.; Maitra, A. K.; Trivedi, H. S. J. Chem. Soc., Chem. Commun. 1979, 984.
337. Schenck, G. O.; Hartmann, W; Steinmetz, R. Chem. Ber. 1963, 96, 498.
338. Toki, S.; Shima, K.; Sakurai, H. Bull. Chem. Soc. Jpn. 1965, 38, 760.
339. Shima, K.; Sakurai, H. Bull. Chem. Soc. Jpn. 1966, 39, 1806.
340. Schreiber, S. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1984, 106, 7200.
341. Rivas, C.; Bolivar, R. A. J. Heterocyclic Chem. 1976, 13, 1037.
342. Jones, G., II; Gilow, H. M.; Low, J. J. Org. Chem. 1979, 44, 2949.
343. Nakano, T.; Rivas, C.; Perez, C.; Larrauri, J. M. J. Heterocyclic Chem. 1976, 13, 173.
344. Nakano, T.; Rodriguez, W.; de Roche, S. Z.; Larrauri, J. M.; Rivas, C.; Perez, C. J. Heterocyclic Chem. 1980, 17, 1777.
345. Julian, D. R.; Tringham, G. D. J. Chem. Soc., Chem. Comm. 1973, 13.
346. Bach, T. Tetrahedron Lett. 1991, 32, 7037.
347. Bach, T. Tetrahedron Lett. 1994, 35, 5845.
348. Bach, T. Liebigs Ann. Chem. 1995, 855.
349. Kotila, S.; Jäntti, A.; Penttinen, S.; Bach, T. Acta Cryst. Sect. C1996, C52, 1722.
350. Zagar, C.; Scharf, H.-D. Chem. Ber. 1991, 124, 967.
351. Jarosz, S.; Zamojski, A. Tetrahedron 1982, 38, 1453.
352. Turro, N. J.; Farrington, G. L. J. Am. Chem. Soc. 1980, 102, 6056.
353. Review: Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem. 1991, 103, 480;
354. Angew. Chem., Int. Ed. Engl. 1991, 30, 477.
355. Gotthardt, H.; Lenz, W. Angew. Chem. 1979, 91, 926;
356. Angew. Chem., Int. Ed. Engl. 1979, 18, 868.
357. Koch, H.; Runsink, J.; Scharf, H.-D. Tetrahedron Lett. 1983, 24, 3217.
358. Koch, H.; Scharf, H.-D.; Runsink, J.; Leismann, H. Chem. Ber. 1985, 118, 1485.
359. Runsink, J.; Koch, H.; Nehrings, A.; Scharf, H.-D.; Nowack, E.; Hahn, T. J. Chem. Soc., Perkin Trans. 2 1988, 49.
360. Weuthen, M.; Scharf, H.-D.; Runsink, J.; Vaßen, R. Chem. Ber. 1988, 121, 971.
361. Pelzer, R.; Jütten, P.; Scharf, H.-D. Chem. Ber. 1989, 122, 487.
362. Pelzer, R.; Scharf, H.-D.; Buschmann, H.; Runsink, J. Chem. Ber. 1989, 122, 1187.
363. Esser, P.; Buschmann, H.; Meyer-Stork, M.; Scharf, H.-D. Angew. Chem. 1992, 104, 1254;
364. Angew. Chem., Int. Ed. Engl. 1992, 31, 1190.
365. Nehrings, A.; Scharf, H.-D.; Runsink, J. Angew. Chem. 1985, 97, 882;
366. Angew. Chem., Int. Ed. Engl. 1985, 24, 877.
367. Oppenländer, T.; Schönholzer, P. Helv. Chim. Acta 1989, 72, 1792.
368. Jarosz, S.; Zamojski, A. Tetrahedron 1982, 38, 1447.
369. Morton, D. R.; Morge, R. A. J. Org. Chem. 1978, 43, 2093.
370. Araki, Y.; Senna, K.; Matsuura, K.; Ishido, Y. Carbohydr. Res. 1978, 60, 389.
371. Vasudevan, S.; Brock, C. P.; Watt, D. S.; Morita, H. J. Org. Chem. 1994, 59, 4677.
372. Bryce-Smith, D.; Gilbert, A. Proc. Chem. Soc. 1964, 87.
373. Bryce-Smith, D.; Gilbert, A.; Johnson, M. G. J. Chem. Soc. C 1967, 383.
374. Ciufolini, M. A.; Rivera-Fortin, M. A.; Zuzukin, V.; Whitmire, K. H. J. Am. Chem. Soc. 1994, 116, 1272.
375. Scharf, D.; Korte, F. Tetrahedron Lett. 1963, 821.
376. Shigemitsu, Y.; Yamamoto, S.; Miyamoto, T.; Odaira, Y. Tetrahedron Lett. 1975, 2819.
377. Sauers, R. R.; Valenti, P. C.; Tavss, E. Tetrahedron Lett. 1975, 3129.
378. Gorman, A. A.; Leyland, R. L.; Parekh, C. T.; Rodgers, M. A. J. Tetrahedron Lett. 1976, 1391.
379. Barwise, A. J. G.; Gorman, A. A.; Leyland, R. L.; Parekh, C. T.; Smith, P. G. Tetrahedron 1980, 36, 397.
380. Bach, T.; Jödicke, K.; Kather, K.; Hecht, J. Angew. Chem. 1995, 107, 2455;
381. Angew. Chem., Int. Ed. Engl. 1995, 34, 2271.
382. Bach, T.; Jödicke, K.; Kather, K.; Fröhlich, R. J. Am. Chem. Soc. 1997, 119, 2437.
383. Bach, T.; Jödicke, K.; Wibbeling, B. Tetrahedron 1996, 52, 10861.
384. Gotthardt, H.; Lenz, W. Tetrahedron Lett. 1979, 2879.
385. Bach, T.; Schröder, J.; Brandi, T.; Hecht, J.; Harms, K. submitted for publication.
386. Hambalek, R.; Just, G. Tetrahedron Lett. 1990, 31, 5445.
387. Nishiyama, S.; Yamamura, S.; Kato, K.; Takita, T. Tetrahedron Lett. 1988, 29, 4743.
388. Schreiber, S. L.; Desmaele, D.; Porco, J. A. Tetrahedron Lett. 1988, 29, 6689.
389. Carless, H. A. J.; Halfhide, A. F. E. J. Chem. Soc., Perkin Trans. 1 1992, 1081.
390. Bach, T.; Schröder, J. Liebigs Ann./Recueil 1997, 2265.
391. Carless, H. A. J.; Fekarurhobo, G. K. J. Chem. Soc., Chem. Commun. 1984, 667.
392. Carless, H. A. J.; Fekarurhobo, G. K. Tetrahedron Lett. 1985, 26, 4407.
393. Reviews: Searles, S. in The Chemistry of Heterocyclic Compounds, Vol. 19-2; Weissberger, A., Ed.; Wiley-Interscience: New York, 1964; pp 983-1068.
394. Searles, S. in Comprehensive Heterocyclic Chemistry, Vol. 7; Katritzky, A. R., Ed.; Pergamon Press: Oxford, 1984; pp 363-402.
395. Brummerhop, H. Diplom Thesis, Universität Marburg, 1997.
396. Bach, T. Tetrahedron Lett. 1994, 55, 1855.
397. Bach, T. Liebigs. Ann. 1995, 1045.
398. Hoye, T. R.; Richardson, W. S. J. Org. Chem. 1989, 54, 688.
399. Bach, T.; Schröder, J. Tetrahedron Lett. 1997, 38, 3707.
400. Bach, T.; Kather, K. J. Prakt. Chem. 1996, 338, 750.
401. Bach, T.; Kather, K.; Krämer, O. J. Org. Chem. 1998, 63, in print.
402. Bach, T.; Lange, C. Tetrahedron Lett. 1996, 37, 4363.
403. Bach, T., Eilers, F.; Kather, K. Liebigs Ann./Recueil 1997, 1529.
404. Schreiber, S. L.; Hoveyda, A. H.; Wu, H. J. J. Am. Chem. Soc. 1983, 105, 660.
405. Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1983, 105, 6723.
406. Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1984, 106, 4186.
407. Schreiber, S. L.; Satake, K. Tetrahedron Lett. 1986, 27, 2575.
408. For applications of this strategy in combination with an intramolecular Paternò-Büchi reaction, see: Rawal, V. H.; Eschbach, A.; Dufour, C.; Iwasa, S. Pure Appl. Chem. 1996, 68, 675.
409. Bach, T.; Kather, K. J. Org. Chem. 1996, 61, 3900.
410. Bach, T.; Eilers, F. manuscript in preparation.
411. Review: Braslavsky, S.; Heicklen, J. Chem. Rev. 1977, 77, 473.
412. Carless, H. A. J. Tetrahedron Lett. 1974, 3425.
413. Shimizu, N.; Nishida, S. J. Chem. Soc., Chem. Commun. 1974, 734.
414. Jones, G., II; Staires, J. C. Tetrahedron Lett. 1974, 2099.
415. Jones, G., II; Aquadro, M. A.; Carmody, M. A. J. Chem. Soc., Chem. Commun. 1975, 206.
416. Carless, H. A. J.; Trivedi, H. S. J. Chem. Soc., Chem. Comm. 1979, 382.
417. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319.