A Tellurium Transposition Route to Allylic Alcohols: Overcoming Some Limitations of the Sharpless-Katsuki Asymmetric Epoxidation

Journal of Organic Chemistry

Volumn 58, Issue 3, 1993, Pages 718-731

  Dittmer, Donald C ^a   Discordia, Robert P ^a   Zhang, Yanzhi ^a   Murphy, Christopher K ^a   Kumar, Archana ^a   Pepito, Aurora S ^a   Wang, Yuesheng ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001211286     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00055a029     Document Type: Article

References (261)

1. Taken in part from Discordia, R. P. Ph.D. Thesis, Syracuse University, 1990. Murphy, C. K. M.S. Thesis, Syracuse University, 1990.
2. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974–5976.
3. Martin, V. S.; Woodaxd, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237–6240.
4. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765–5780.
5. Johnson, R. A.; Sharpless, K. B. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 7, Chapter 3.2. We thank Professor Sharpless for providing us with a copy in advance of publication
6. Rossiter, B. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985, Vol. 5, pp 193–246.
7. Finn, M. G.; Sharpless, K. B. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, pp 247–308.
8. Sharpless, K. B.; Behrens, C. H.; Katsuki, T.; Lee, A. W. M.; Martin, V. S.; Takatani, M.; Viti, S. M.; Walker, F. J.; Woodard, S. S. Pure Appl. Chem. 1983, 55, 589–604.
9. Davis, F. A.; Thimma Reddy, R. J. Org. Chem. 1992, 57, 2599–2606.
10. Poison, G.; Dittmer, D. C. Tetrahedron Lett. 1986, 27, 5579–5582.
11. Poison, G. Ph.D. Thesis, Syracuse University, 1987.
12. Discordia, R. P.; Dittmer, D. C. J. Org. Chem. 1990, 55, 1414–1415.
13. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31, 5603–5606.
14. Discordia, R. P.; Dittmer, D. C. U.S. Pat. 4,935,451, June 19, 1990;
15. Chem. Abstr. 1990, 113, 190736.
16. Dittmer, D. C.; Murphy, C. K.; Discordia, R. P. U.S. Pat. 5,087,773, Feb 11, 1992;
17. Chem. Abstr. 1992, 116, 235070.
18. Sax, N. I.; Lewis, R. J. Dangerous Properties of Industrial Materials; Van Nostrand Reinhold: New York, 1989, Vol. III; p 3131.
19. Sittig, M. Handbook of Toxic and Hazardous Chemicals and Carcinogens, 2nd ed.; Noyes: Park Ridge, NJ, 1985; pp 828–829.
20. Reduction of Te by rongalite: Tschugaeff, L.; Chlopin, W. Ber. 1914, 47, 1269–1275.
21. Clive, D. L. J.; Menchen, S. M. J. Org. Chem. 1980, 45, 2347–2354.
22. Bäckvall, J.-E.; Engman, L. Tetrahedron Lett. 1981, 22, 1919–1922.
23. Clive, D. L. J.; Beaulieu, P. L. J. Org. Chem. 1982, 47, 1124–1126.
24. Barton, D. H. R.; Fekih, A.; Lusinchi, X. Tetrahedron Lett. 1985, 26, 6197–6200.
25. Zingaro, R. A.; Herrera, C. Bull. Chem. Soc. Jpn. 1989, 62, 1382–1384.
26. Connor, J.; Greig, G.; Strausz, O. P. J. Am. Chem. Soc. 1969, 91, 5695–5696.
27. Schäfer, A.; Weidenbruch, M.; Saak, W.; Pohl, S.; Marsmann, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 834–836.
28. We are indebted to Dr. Douglas A. Livingstone for suggesting this terminology. Some other examples of nucleophilic reductions involving Te: Yamashita, M.; Kato, Y.; Suemitsu, R. Chem. Lett. 1980, 847–848.
29. Kambe, N.; Kondo, K.; Morita, S.; Murai, S.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1980, 19, 1009.
30. Osuka, A.; Suzuki, H. Chem. Lett. 1983, 119–120.
31. Osuka, A.; Taka-oka, K.; Suzuki, H. Chem. Lett. 1984, 271–272.
32. Barton, D. H. R.; Fekih, A.; Lusinchi, X. Tetrahedron Lett. 1985, 26, 3693–3696.
33. Huang, X.; Pi, J.-H. Synth. Commun. 1990, 20, 2297–2300.
34. Payne, G. B. J. Org. Chem. 1962, 27, 3819–3822.
35. Wood, W. F.; Fesler, M. J. Chem. Ed. 1986, 63, 92.
36. Mosandl, A.; Heusinger, G.; Gessner, M. J. Agric. Food Chem. 1986, 34, 122–126.
37. Helmchen, G.; Ihrig, K.; Schindler, H. Tetrahedron Lett. 1987, 28 183–186.
38. Pross, A. Adv. Phys. Org. Chem. 1985, 21, 99–196.
39. Pross, A. Acc. Chem. Res. 1985, 18, 212–219.
40. Pross, A.; Shaik, S. S. Acc. Chem. Res. 1983, 16, 363–370.
41. Shaik, S. S. J. Am. Chem. Soc. 1983, 105, 4359–4367.
42. Cyclodextrins have been used to improve regioselectivity of nucleophilic ring opening of styrene oxide: Hu, Y.; Uno, M.; Haroda, A.; Takahashi, S. Chem. Lett. 1990, 797–798.
43. Brown, H. C.; Heim, P. J. Org. Chem. 1973, 38, 912–916.
44. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129–6139.
45. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1990, 112, 7434–7436.
46. Schweiter, M. J.; Sharpless, K. B. Tetrahedron Lett. 1985, 26, 2543–2546.
47. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645–5648.
48. Wang, Z.; Zhou, W. Tetrahedron 1987, 43, 2935–2944.
49. Wang, Z.; Zhou, W. Synth. Commun. 1989, 19, 2627–2632.
50. Takano, S.; Iwabuchi, Y.; Ogasawara, K. Tetrahedron Lett. 1991, 32, 3527–3528.
51. Erickson, T. J. J. Org. Chem. 1986, 51, 934–935.
52. Barner, R.; Hübscher, J. Helv. Chim. Acta 1983, 66, 880–890.
53. Ohwa, M.; Kogure, T.; Eliel, E. L. J. Org. Chem. 1986, 51, 2599–2601.
54. Landolt, P. J.; Heath, R. R. Science 1990, 249, 1026–1028.
55. Cooke, F.; Roy, G.; Magnus, P. Organometallics 1982, 1, 893–897.
56. Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25–28.
57. Gonnella, N. C.; Nakanishi, K.; Martin, V. S.; Sharpless, K. B. J. Am. Chem. Soc. 1982, 104, 3775–3776.
58. Bierl-Leonhardt, B. A.; Moreno, D. S.; Schwarz, M.; Forster, H. S.; Plimmer, J. R.; DeVilbiss, E. D. Life Sci. 1980, 27, 399–402.
59. Bierl-Leonhardt, B. A.; Moreno, D. S.; Schwarz, M.; Forster, H. S.; Plimmer, J. R.; DeVilbiss, E. D. J. Chem. Ecol. 1982, 8, 689–699.
60. Negishi, T.; Uchida, M.; Tamaki, Y.; Mori, K.; Ishiwatari, T.; Asano, S.; Nakagawa, K. Appl. Entomol. Zoolog. 1980, 15, 328–333.
61. Uchida, M.; Nakagawa, K.; Negishi, T.; Asano, S.; Mori, K. Agric. Biol. Chem. 1981, 45, 369–372.
62. Nakagawa, N.; Mori, K. Agric. Biol. Chem. 1984, 48, 2799–2803.
63. Mori, K.; Ueda, H. Tetrahedron 1981, 37, 2581–2583.
64. Ronald, R. C.; Ruder, S. M.; Lillie, T. S. Tetrahedron Lett. 1987, 28, 131–134.
65. Overman, L. E.; Lin, H.-H. J. Org. Chem. 1985, 50, 3670–3672.
66. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719–2722.
67. Nicolaou, K. C.; Uenishi, J. J. Chem. Soc., Chem. Commun. 1982, 1292–1293.
68. Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170–173.
69. Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1991, 32, 5777–5780.
70. For a list of both types of isomerization, see: Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; p 109.
71. March, J. Advanced Organic Chemistry, 3rd ed.; Wiley: New York, 1985; p 920.
72. Cuvigny, T.; du Penhoat, C. H.; Julia, M. Recl. Trav. Chim. Pays-Bas 1986, 105, 409–421.
73. 1H NMR spectrum at consistently higher field than that of the erythro isomers. This may be the result of the formation of a more stable intramolecular hydrogen bond between the hydroxyl group and the epoxide oxygen in the threo isomer because of less steric congestion as indicated by models. Conversion of the threo and erythro glycidols to their tosylates reverses the shielding of the methine proton; this proton in the erythro isomer now resonates at higher field than that in the threo isomer. This may be due to a smaller dipole moment of the erythro tosylate expected from consideration of the lowest energy rotamer. [For a discussion of the rotamer energies of glycidols, see: Roush, W. R.; Brown, R. J.; DiMare, M. J. Org. Chem. 1983, 48, 5083–6093.]
74. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1985, 107, 766–773.
75. Miyashita, M.; Hoshino, M.; Yoshikoshi, A. Tetrahedron Lett. 1988, 29, 347–350.
76. Miyashita, M.; Hoshino, M.; Suzuki, T.; Yoshikoshi, A. Chem. Lett. 1988, 507–608.
77. Parish, E. J.; Schroepfer, G. J., Jr. Tetrahedron Lett. 1976, 3775–3778.
78. Zaidlewicz, M.; Uzarewicz, A.; Sarnowski, R. Synthesis 1979, 62–64.
79. Lenox, R. S.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1973, 95, 957–959.
80. Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378–1380.
81. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719–2722.
82. Viti, S. M. TetrahedronLett. 1982, 23, 4541–4544.
83. Kirshenbaum, K. S.; Sharpless, K. B. Chem. Lett. 1987, 11–14.
84. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560–1563.
85. Onaka, M.; Sugita, K.; Takeuchi, H.; Izumi, Y. J. Chem. Soc., Chem. Commun. 1988, 1173.
86. Some of these rearrangements are summarized in a useful compendium: Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; pp 114–119, 191, 480, 581.
87. Fujita, E.; Shibuya, M.; Nakamura, S.; Okada, Y.; Fujita, T. J. Chem. Soc., Perkin Trans. 1 1974, 165–177.
88. Stork, G.; Nakahara, Y.; Nakahara, J.; Greenlee, W. J. J. Am. Chem. Soc. 1978, 100, 7775–7777.
89. Kigoshi, H.; Ojika, M.; Shizuri, Y.; Niwa, H.; Yamada, K. Tetrahedron Lett. 1982, 23, 5413–5414.
90. Nicolaou, K. C.; Duggan, M. E.; Laddu-wahetty, T. Tetrahedron Lett. 1984, 25, 2069–2072.
91. Kigoshi, H.; Ojika, M.; Shizuri, Y.; Niwa, H.; Yamada, K. Tetrahedron 1986, 42, 3789–3792.
92. Singh, A. K.; Bakshi, R. K.; Corey, E. J. J. Am. Chem. Soc. 1978, 109, 6187–6189.
93. Corey, L. D.; Singh, S. M.; Oehlschlager, A. C. Can. J. Chem. 1987, 65, 1821–1827.
94. Barluenga, J.;Concellon, J. M.; Fernandez-Simon, J. L.; Yus, M. J. Chem. Soc., Chem. Commun. 1988, 536–537.
95. Marshall, J. A.; Sedrani, R. J. Org. Chem. 1991, 56, 5496–5498.
96. Bartok, M.; Lang, K. L. Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1985; Part 3; pp 62–65.
97. Crandall, J. K.; Apparu, M. Org. React. 1983, 29, 345–443.
98. Takano, S.; Samizu, K.; Sugihara, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 1344–1345.
99. Takano, S.; Sugihara, T.; Samizu, K.; Akiyama, M.; Ogasawara, K. Chem. Lett. 1989, 1781–1784.
100. Yadav, J. S.; Deshpande, P. K.; Sharma, G. V. M. Tetrahedron Lett. 1990, 31, 4495–4496.
101. Whitesell, J.K.;Felman, S. W. J. Am. Chem. Soc 1980, 102, 755–756.
102. Mori, K.; Hazra, B. G.; Pfeiffer, R. J.; Gupta, A. K.; Lindgren, B. S. Tetrahedron Lett. 1987, 43, 2249–2254.
103. Asami, M.; Kanemaki, N. Tetrahedron Lett. 1989, 30, 2125–2128.
104. Fürstner, A.; Weidmann, H. J. Org. Chem. 1989, 54, 2307–2311.
105. Fürstner, A.; Weidmann, H. J. Org. Chem. 1990, 55, 1363–1366.
106. Fürstner, A. Tetrahedron Lett. 1990, 31, 3735–3738.
107. Roush, W. R.; Grover, P. T. Tetrahedron Lett. 1990, 31, 7567–7570.
108. Matsumoto, T.; Kitano, Y.; Sato, F. Tetrahedron Lett. 1988, 29, 5685–5688.
109. Marshall, J. A.; Hagan, C. P.; Flynn, G. A. J. Org. Chem. 1975, 40, 1162–1166.
110. Marshall, J. A.; Ellison, R. H. J. Am. Chem. Soc 1976, 98, 4312–4313.
111. Yasuda, A.; Yamamoto, H.; Nozaki, H. Tetrahedron Lett. 1976, 2621–2622.
112. Yasuda, A.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 1757–1759.
113. Kocienski, P. J.; Tideswell, J. Synth. Commun. 1979, 9, 411–418.
114. Yadav, J. S.; Shekharam, T.; Gadgil, V. R. J. Chem. Soc., Chem. Commun. 1990, 843–844.
115. Nugent, W. A.; Rajan Babu, T. V. J. Am. Chem. Soc 1988, 110, 8561–8562.
116. Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106–5107.
117. Barton, D. H. R.; Motherwell, R. S. H.; Motherwell, W. B. J. Chem. Soc., Perkin Trans. 1 1981, 2363–2367.
118. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181–5183.
119. Sarandeses, L. A.; Mourino, A.; Luche, J.-L. J. Chem. Soc., Chem. Commun. 1991, 818–820.
120. March, J. Advanced Organic Chemistry, 3rd ed.; Wiley: New York, 1985; p 289.
121. Kitching, W.; Rappoport, Z.; Winstein, S.; Young, W. G. J. Am. Chem. Soc 1966, 88, 2054–2055.
122. Henry, P. M. J. Am. Chem. Soc. 1972, 94, 5200–5206.
123. Overman, L. E.; Campbell, C. B.; Knoll, F. M. J. Am. Chem. Soc. 1978, 100, 4822–4834.
124. Ichinohe, Y.; Sakamaki, H.; Kameda, N. Chem. Lett. 1978, 835–838.
125. Jung, M. E.; McCoombs, C. A. J. Am. Chem. Soc 1978, 100, 5207–6209.
126. Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321–324.
127. Tsai, T. Y. R.; Minta, A.; WieBner, K. Heterocycles 1979, 12, 1397–1402.
128. Golding, B. T.; Pierpont, C.; Aneja, R. J. Chem. Soc., Chem. Commun. 1981, 1030–1031.
129. Takatsuto, S.; Ishiguro, M.; Ikekawa, N. J. Chem. Soc., Chem. Commun. 1982, 258–260.
130. Oehlschlager, A. C.; Mishra, P.; Dhami, S. Can. J. Chem. 1984, 62, 791–797.
131. Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579–586.
132. Saito, S.; Hamano, S.; Moriyama, H.; Okada, K.; Moriwake, T. Tetrahedron Lett. 1988, 29, 1157–1160.
133. Panek, J. S.; Sparks, M. A. J. Org. Chem. 1990, 55, 5564–5566.
134. Ueno, Y.; Sano, H.; Okawara, M. Synthesis 1980, 1011–1013.
135. Schenck, G. D.; Neumüller, O. A.; Eisfeld, W. Justus Liebig's Ann. Chem. 1958, 618, 202–210.
136. Brill, W. F. J. Am. Chem. Soc. 1965, 87, 3286–3287.
137. Brill, W. F. J. Chem. Soc., Perkin Trans. 2 1984, 621–627.
138. Porter, N. A.; Kaplan, J. K.; Dussault, P. H. J. Am. Chem. Soc 1990, 112, 1266–1267.
139. Corey, E. J.; Su, W.; Mehrotra, M. M. Tetrahedron Lett. 1984, 25, 5123–5126.
140. Bickart, P.; Carson, F. W.; Jacobus, J.; Miller, E. G.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4869–4876.
141. Abbott, D. J.; Stirling, C. J. M. J. Chem. Soc. C 1969, 818–821.
142. Evans, D. A.; Andrews, G. C.; Sims, C. L. J. Am. Chem. Soc. 1971, 93, 4956–4957.
143. Grieco, P. A. J. Chem. Soc., Chem. Commun. 1972, 702.
144. Evans, D. A.; Andrews, G. C.; Fujimoto, T. T.; Wells, D. Tetrahedron Lett. 1973, 1385–1388, 1389–1392.
145. Evans, D. A.; Andrews, G. C. Acc Chem. Res. 1974, 7, 147–155.
146. Miller, J. G.; Kurz, W.; Untch, K. G.; Stork, G. J. Am. Chem. Soc. 1974, 96, 6774–6775.
147. Hoffmann, R. W.; Maak, N. Tetrahedron Lett. 1976, 2237–2240.
148. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1979, 18, 563–572.
149. Hoffmann, R. W.; Goldmann, S.; Gerlach, R.; Maak, N. Chem. Ber. 1980, 113, 845–853.
150. Guittet, E.; Julia, S. Synth. Commun. 1981, 11, 723–732.
151. Brown, W. L.; Fallis, A. G. Tetrahedron Lett. 1985, 26, 607–610.
152. Brown, W. L.; Fallis, A. G. Can. J. Chem. 1987, 65, 1828–1832.
153. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1989, 54, 2779–2780.
154. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1972, 94, 7154–7155.
155. Sharpless, K. B.; Young, M. W.; Lauer, R. F. Tetrahedron Lett. 1973, 1979–1982.
156. Reich, H. J. J. Org. Chem. 1975, 40, 2570–2572.
157. Salmond, W. G.; Barta, M. A.; Cain, A. M.; Sobala, M. C. Tetrahedron Lett. 1977, 1683–1686.
158. Kametani, T.; Nemoto, H.; Fukumoto, K. Heterocycles 1977, 6, 1365–1370.
159. Clive, D. L. J.; Chittattu, G.; Curtis, N. J.; Menchen, S.M.J. Chem. Soc., Chem. Commun. 1978, 770–771.
160. Nishiyama, H.; Itagaki, K.; Sakuta, K.; Itoh, K. Tetrahedron Lett. 1981, 5285–5288.
161. Zoretic, P. A.; Chambers, R. J.; Marbury, G. D.; Riebiro, A. A. J. Org. Chem. 1985, 50, 2981–2987.
162. Davis, F. A.; Stringer, O. D.; McCauley, J. P., Jr. Tetrahedron 1985, 41, 4747–4757.
163. Reich, H. J.; Yelm, K. E. J. Org. Chem. 1991, 56, 5672–5679.
164. Uemura, S.; Fukuzawa, S.; Ohe, K. Tetrahedron Lett. 1985, 26, 921–924.
165. Yakamoto, S.; Itarii, H.; Tsuji, T.; Nagata, W. J. Am. Chem. Soc. 1983, 105, 2908–2909.
166. Ichikawa, Y. Synlett 1991, 238–240.
167. Chabardes, P.; Kuntz, E.; Varagnat, J. Tetrahedron 1977, 33, 1775–1783.
168. Hosogai, T.; Fujita, Y.; Ninagawa, Y.; Nishida, T. Chem. Lett. 1982, 357–360.
169. Matsubara, S.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1983, 24, 3741–3744.
170. Matsubara, S.; Okazoe, T.; Oshima, K.; Takai, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 844–849.
171. Gulyi, S. E.; Novikov, N. A.; Erman, M. B. J. Org. Chem. USSR 1986, 22, 1404.
172. Suryawanshi, S. N.; Rani, A.; Bhakuni, D. S. Synth. Commun. 1990, 20, 625–632.
173. Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682–685.
174. Meisenheimer, J. Chem. Ber. 1919, 52, 1667–1677.
175. Rautenstrauch, V. Helv. Chim. Acta 1973, 56, 2492–2508.
176. Wharton, P. S.; Bohlen, D. H. J. Org. Chem. 1961, 26, 3615–3616.
177. Ohloff, G.; Uhde, G. Helv. Chim. Acta 1970, 53, 531–541.
178. Isaeva, Z. G.; Karaseva, A. N.; Ikhtonova, I. S. Bull. Acad. Sci. USSR Ser. Chim. 1985, 2435–2436.
179. Baeckstrom, P.; Li, L. Synth. Commun. 1990, 20, 1481–1485.
180. Büchi, G.; Vederas, J. C. J. Am. Chem. Soc. 1972, 94, 9128–9132.
181. Stork, G.; Williard, P. G. J. Am. Chem. Soc. 1977, 99, 7067–7068.
182. Paquette, L. A.; Ham, W. H. J. Am. Chem. Soc. 1987, 109, 3025–3036.
183. Dasaradhi, L.; Neelakantan, P.; Jagadishwar, S.; Bhalerao, U. T. Synth. Commun. 1991, 21, 183–190.
184. Schulte-Elte, K. H.; Müller, B. L.; Ohloff, G. Helv. Chim. Acta 1973, 56, 310–320.
185. Poison, G.; Dittmer, D. C. J. Org. Chem. 1988, 53, 791–794.
186. For reviews on Te chemistry, see the following: Engman, L. Acc. Chem. Res. 1985, 18, 274–279.
187. Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1–30.
188. Patai, S., Rappoport, Z., Eds. The Chemistry of Organic Selenium and Tellurium Compounds; Wiley: Chichester, U.K., 1986; Vol. 1.
189. Patai, S., Ed.; The Chemistry of Organic Selenium and Tellurium Compounds; Wiley: Chichester, U.K., 1987; Vol. 2.
190. Sadekov, I. D.; Rivkin, B. B.; Minkin, V. I. Russ. Chem. Rev. 1987, 56, 586–608.
191. Engman, L. Phosphorus Sulfur 1988, 38, 105–119.
192. Irgolic, K. J. Methods of Organic Chemistry (Houben-Weyl), Organotellurium Compounds; Klamann, D., Ed.; G. Theime: Stuttgart, 1990; Vol. E 12 b.
193. Petragnani, N.; Comasseto, J. V. Synthesis, 1991, 793–817, 897–919.
194. Jarvis, W. F.; Hoey, M. D.; Finocchio, A. L.; Dittmer, D. C. J. Org. Chem. 1988, 53, 5750–5756 and references cited therein
195. Hoey, M. D.; Dittmer, D. C. J. Org. Chem. 1991, 56, 1947–1948.
196. The United States Pharmacopeial Convention, The United States Pharmacopeia/The National Formulary, USP XXII/NF XVII; Mack: Easton, PA, 1989; p 1979.
197. Tibbals, C. A., Jr. J. Am. Chem. Soc. 1909, 31, 902–913.
198. McCleary, R. L.; Fernelius, W. C. J. Am. Chem. Soc. 1934, 56, 803–804.
199. Suzuki, H.; Inouye, M. Chem. Lett. 1986, 403–406.
200. Barton, D. H. R.; Bohe, L.; Lusinchi, X. Tetrahedron 1990, 46, 5273–5284.
201. Discordia, R. P.; Dittmer, D. C. Tetrahedron Lett. 1988, 29, 4923–4926.
202. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543–2549.
203. Goering, H. L.; Eikenberry, J. N.; Koermer, G. S.; Lattimer, C. J. J. Am. Chem. Soc. 1974, 96, 1493–1501.
204. Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506–2526.
205. Chen, J.; Zhou, X. J. Synthesis 1987, 18, 586–587.
206. Gladysz, J. A.; Hornby, J. L.; Garbe, J. E. J. Org. Chem. 1978, 43, 1204–1208.
207. Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641–1647.
208. Luché, J.-L. J. Am. Chem. Soc. 1978, 100, 2226–2227.
209. Luché, J.-L.; Rodriguez-Hahn, L.; Crabbe, P. J. Chem. Soc., Chem. Commun. 1978, 601–602.
210. 13C NMR 1726.
211. Grünanger, P.; Grieco, D. Gazz. Chim. Ital. 1958, 88, 296–307.
212. Thijs, L.; Waanders, P. P.; Stokkingreef, E. H. M.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1986, 105, 332–337.
213. Tsuboi, S.; Furitani, H.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 833–835.
214. Mulzer, J.; Lammer, O. Chem. Ber. 1986, 119, 2178–2190.
215. Kang, S.-K.; Kim, Y.-S.; Lim, J.-S.; Kim, K.-S.; Kim, S.-G. Tetrahedron Lett. 1991, 32, 363–366.
216. Ennis, M. D.; Baze, M. E. Tetrahedron Lett. 1986, 27, 6031–6034.
217. Zamboni, R.; Milette, S.; Rokach, J. Tetrahedron Lett. 1983, 24, 4899–4902
218. Martin, V. S.; Nunez, M. T.; Tonn, C. E. Tetrahedron Lett. 1988, 29, 2701–2702.
219. Huang, D.-F.; Huang, L. Tetrahedron 1990, 46, 3135–3142.
220. Takano, S.; Yanase, M.; Ogasawara, K. Heterocycles 1989, 29, 249–252.
221. Palazon, J. M.; Aftorbe, B.; Martin, V. S. Tetrahedron Lett. 1986, 27, 4987–4990.
222. Wang, Z.-M.; Zhou, W.-S. Tetrahedron 1987, 43, 2935–2944.
223. Melloni, P.; Della Torre, A.; Lazzari, E.; Mazzini, G.; Meroni, M. Tetrahedron 1985, 41, 1393–1399.
224. Brunner, H.; Sicheneder, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 718–719.
225. Duveen, D. I.; Kenyon, J. J. Chem. Soc. 1939, 1697–1701.
226. Arcus, C. L.; Strauss, H. E. J. Chem. Soc. 1952, 2669–2671.
227. Kurth, M. J.; Decker, O. H. W. J. Org. Chem. 1985, 50, 5769–5775.
228. Takano, S.; Mishizawa, S.; Akiyama, M.; Ogasawara, K. Heterocycles 1984, 22, 1779–1788.
229. Rao, A. V. R.; Bose, D. S.; Gurjar, M. K.; Ravindranathan, T. Tetrahedron 1989, 45, 7031–7040.
230. Nicolaou, K. C.; Daines, R. A.; Ueniahi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. J. Am. Chem. Soc 1988, 110, 4672–4685.
231. Roush, W. R.; Adam, M. A.; Peseckis, S. M. Tetrahedron Lett. 1983, 24, 1377–1380.
232. Soulie, J.; Lampilas, M.; Lallemand, J. Y. Tetrahedron 1987, 43, 2701–2708.
233. Takano, S.; Kasahara, C.; Ogasawara, K. Chem. Lett. 1983, 175–176.
234. Katsuki, T.; Lee, A. W. M.; Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1373–1378.
235. Hungerbühler, E.; Seebach, D. Helv. Chim. Acta 1981, 64, 687–702.
236. Takano, S.; Shun'ichi, T.; Iwabuchi, Y.; Ogasawara, K. Synthesis 1988, 610–611.
237. Rao, A. V. R.; Reddy, E. R.; Joshi, B. V.; Yadev, J. S. Tetrahedron Lett. 1987, 28, 6497–6500.
238. Majetich, G.; Casare, A.; Chapman, D.; Behnke, M. J. Org. Chem. 1986, 51, 1745–1753.
239. Kopecky, K. R.; Levine, C. Can. J. Chem. 1981, 59, 3273–3279.
240. Georgoulis, C.; Smadja, W.; Ville, G. Bull. Soc. Chim. Fr. 1984, 269–270.
241. Nozoe, S.; Koike, Y.; Kusano, G. Tetrahedron Lett. 1984, 25, 1371–1372.
242. Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agnani, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353–2357.
243. Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391–402.
244. Gill, M.; Smrdel, A. F. Tetrahedron Asymm. 1990, 1, 453–464.
245. Yamamoto, K.; Ando, H.; Shuetake, T.; Chikamatsu, H. J. Chem. Soc., Chem. Commun. 1989, 754–755.
246. Ohloff, G.; Giersch, W.; Schulte-Elte, K. H.; Enggist, P.; Demole, E. Helv. Chim. Acta 1980, 63, 1582–1588.
247. Wilson, W. K.; Scallen, T. J.; Morrow, C. J. J. Lipid Res. 1982, 23, 645–652.
248. Hiraga, Y.; Izumi, S.; Hirata, T.; Suga, T. Chem. Lett. 1991, 49–52.
249. Ohloff, G.; Klein, E. Tetrahedron 1962, 18, 37–42.
250. Tanaka, N.; Sakai, H.; Murakami, T.; Saiki, Y.; Chen, C.; Iitaka, Y. Chem. Pharm. Bull. 1986, 34, 1015–1022.
251. del Castillo, J.B.; Brooks, C. J. W.; Campbell, M. M. Tetrahedron Lett. 1966, 3731–3736.
252. Vlad, P.; Soucek, M. Collect. Czech. Chem. Commun. 1962, 27, 1726–1729.
253. Cane, D. E.; Ha, H.-J.; McIlwane, D. B.; Pascoe, K. O. Tetrahedron Lett. 1990, 52, 7553–7554.
254. Hayashi, M.; Terashima, S.; Koga, K. Tetrahedron 1981, 37, 2797–2803.
255. Goodwin, T. E.; Ratcliffe, D. G.; Crowder, C. M.; Seitzinger, N. K. J. Org. Chem. 1982, 47, 815–820.
256. Oshima, M.; Yamazaki, H.; Shimizu, I.; Nisar, M.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 6280–6287.
257. Braude, E. A.; Evans, E. A. J. Chem. Soc. 1956, 3333–3337.
258. Stevens, P. G.; Allenby, O. C. W.; DuBois, A. S. J. Am. Chem. Soc. 1940, 62, 1424–1428.
259. Lythgoe, B.; Trippett, S.; Watkins, J. C. J. Chem. Soc. 1956, 4060–4065.
260. Kurth, M. J.; Beard, R. L. J. Org. Chem. 1988, 53, 4085–4088.
261. Kaufman, T. S.; Sindelar, R. D. J. Heterocycl. Chem. 1989, 26, 879–881.