Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond

Tetrahedron Asymmetry

Volumn 8, Issue 12, 1997, Pages 1895-1946

  Enders, Dieter ^a   Reinhold, Ulrich ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b Knoll AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HYDRAZONE DERIVATIVE; IMINE; NITRO DERIVATIVE; ORGANOMETALLIC COMPOUND; OXIME DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030924784     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00208-5     Document Type: Review

References (191)

1. For excellent general reviews about nucleophilic alkylation of the C=N bond see: a) Risen, N.; Arend, M. In: Methods of Organic Chemistry (Houben-Weyl): Stereoselective Synthesis; Helmchen. G. Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag, Stuttgart; 1995, Vol. E 21b, p. 1883.
2. b) Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon, New York, 1991; Vol. 1, p. 355. Recent review about ligand-mediated addition: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. For reviews about nucleophilic allylation of the C=N bond see:
3. b) Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon, New York, 1991; Vol. 1, p. 355. Recent review about ligand-mediated addition: Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. For reviews about nucleophilic allylation of the C=N bond see:
4. a) Risch, N.; Arend, M. [1a], p. 1894. Roush, W. R, [1a], Vol. 2, p. 1.
5. a) Risch, N.; Arend, M. [1a], p. 1894. Roush, W. R, [1a], Vol. 2, p. 1.
6. b) Kleinmann, E. F.; Volkmann, R. A. [1a], Vol. 2, p. 975.
7. c) Yamamoto, Y.; Asao, N. Chem, Rev. 1993, 93, 2207. For a short overview about asymmetric synthesis of amines see: Johansson, A. Contemporary Organic Synthesis 1995, 2, 393. For the stereoselective synthesis of α-amino acids see also:
8. c) Yamamoto, Y.; Asao, N. Chem, Rev. 1993, 93, 2207. For a short overview about asymmetric synthesis of amines see: Johansson, A. Contemporary Organic Synthesis 1995, 2, 393. For the stereoselective synthesis of α-amino acids see also:
9. a) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
10. b) Williams, R. M. Aldrichimica Acta 1992, 25, 11.
11. c) Williams, R. M. In Synthesis of Optically Active Amino acids, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon, 1989, New York, N.Y.; Vol. 7. For reviews about stereoselective synthesis of β-amino acids and β-lactams see:
12. a) Cole, D. C. Tetrahedron 1994, 50, 9517.
13. b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichimica Acta 1994, 27, 3.
14. c) Enantioselective Synthesis of β-Amino Acids; Juraristi, E., Ed.; Wiley-VCH Publishers, New York, 1997.
15. d) Williams, R. M. Aldrichimica Acta 1992, 25, 11.
16. e) Hart, D. J.; Ha. D.-C. Chem. Rev. 1989, 89, 1447.
17. In spite of our intensive literature search to gather all relevant publications we want to apologize to the research groups whose work are not mentioned in this paper. We would be very pleased if the researchers inform us about missing papers.
18. Review about stereoselective addition to N-acyliminium ions: a) de Koning, H.; Speckamp, W. N. [1a], p. 1953.
19. b) Hiemstra, H.; Speckamp, W. N. [1b], Vol. 2, p. 1047. Mannich-type reaction:
20. c) Kleinman E. F. [1b], Vol. 2, p. 893.
21. d) Heaney, H. [1b], Vol. 2, p. 953.
22. d) Overman, L. E.; Ricca, D. J. [1b], Vol. 2, p.1007. Aldol-type reaction:
23. e) Risch, N.; Arend, M. [1a], p. 1894.
24. f) Gennari, C. [1b], Vol. 2, p. 629. Strecker and Ugi reaction:
25. g) Kunz, H. [1a], p. 1931,
26. h) Ugi, I.; Lohberger, S.; Karl, R. [1b], Vol. 2, p. 1083.
27. a) Takahashi, H.; Suzuki, Y.; Inagaki, H. Chem. Pharm. Bull. 1982, 30, 3160.
28. b) Suzuki, Y; Takahashi, H Chem. Pharm. Bull. 1983, 31, 31 and 2895.
29. c) Takahashi, H.; Chida, Y.; Suzuki, T.; Yanaura, S.; Suzuki, Y.; Masuda, C. Chem. Pharm. Bull. 1983, 31, 1659.
30. d) Takahashi, H.; Suzuki, Y; Hori, T. Chem. Pharm. Bull. 1983, 31, 2183.
31. e) Takahashi, H.; Chida, Y.; Yoshii, T.; Suzuki, T.; Yanaura, S. C. Chem. Pharm. Bull. 1986, 34, 12071.
32. a) Wu, M.-J.; Pridgen, L. N. Synlett 1990, 636.
33. b) Wu, M.-J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340.
34. c) Pridgen, L. D.; Mokhallalati, M. K.; Wu, M.-J. J. Org. Chem. 1992, 57, 1237.
35. d) Mokhallalati, M. K.; Pridgen, L. N. Synth. Commun. 1993, 23, 2055.
36. e) Muralidharan, K. R.; Mokhallalati, M. K.; Pridgen, L. N. Tetrahedron Lett. 1994, 35, 7489.
37. f) Pridgen, L. D.; Mokhallalati, M. K.; McGuire, M. A. Tetrahedron Lett. 1997, 38, 1275.
38. Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1993, 1542.
39. a) Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron Lett. 1992, 33, 235.
40. b) Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron 1994, 50, 1083.
41. c) Higashiyama, K.; Inoue, H.; Yamauchi, T. Takahashi, H. J. Chem. Soc., Perkin Trans. 1 1995, 111.
42. Miao, C. K.; Sorcek, R.; Jones, R.-J. Tetrahedron Lett. 1993, 34, 2259.
43. Chen, L.; Trilles, R. V.; Tilley, J. W. Tetrahedron Lett. 1995, 36, 8715.
44. Ukaji, Y.; Watai, T.; Sumi, T.; Fujisawa, T. Chem. Lett. 1991, 1555.
45. Higashiyama, K.; Fujikura, H.; Takahashi, H. Chem. Pharm. Bull. 1995, 43, 722.
46. Betz, J.; Heuschmann, M. Tetrahedron Lett. 1995, 36, 4043.
47. Hashimoto, Y.; Takaoki, K.; Sudo, A.; Ogasawara, T.; Saigo, K. Chem. Lett. 1995, 235.
48. Harwood, K. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051.
49. Tanaka, H.; Inoue, K.; Pokorski, U.; Taniguchi, M.; Torii, S. Tetrahedron Lett. 1990, 31, 3023.
50. Giammaruco, M.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1993, 34, 3635.
51. Bhuyan, P. J.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1993, 34, 7975.
52. a) Basile, T.; Bocoum, A.; Savoia, D, Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
53. b) Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083.
54. c) Bocoum, A.; Basile, T.; Savoia, D, Umani-Ronchi, A. Tetrahedron Lett. 1991, 32, 1367.
55. Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289.
56. Loh, T.-P.; Ho, D. S.-C.; Xu, K.-C.; Sim, K.-Y. Tetrahedron Lett. 1997, 35, 865.
57. Waldmann, H.; Braun., M.; J. Org. Chem. 1992, 57, 4444.
58. a) Dembélé, Y. A.; Belaud, C.; Villiéras, J. Tetrahedron: Asymmetry 1992, 3, 351.
59. b) Nyzam, V; Belaud, B.; Zammattio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 7, 1835.
60. c) Dembélé, Y. A.; Belaud, C.; Villiéras, J. Tetrahedron: Asymmetry 1992, 3, 511.
61. Uno, H.; Okada, S.; Ono, T.; Shiraishi, Y.; Suzuki, H. J. Org. Chem. 1992, 57, 1504.
62. a) Yamamoto, Y.; Konatsu, T.; Maruyama, K. J. Am. Chem. Soc. 1984, 106, 5031.
63. b) Yamamoto, Y.; Nishii, S.; Maruyama, K. Komatsu, T.; Itoh, W. J. Am. Chem. Soc. 1986, 108, 7778.
64. Beuchet, P.; Le Marrec, N.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
65. a) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649.
66. b) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4188.
67. Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136.
68. Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc., Perkin Trans. 1 1996, 875.
69. a) Yamamoto, Y; Ito, W.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 1131.
70. b) Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415.
71. Hallett, D. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1995, 657.
72. Neumann, W. L.; Rogic, M. M.; Dunn, T. J. Tetrahedron Lett. 1991, 32, 5865.
73. Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
74. a) Boga, C.; Savoia, D.; Umani-Ronchi, A. Tetrahedron: Asymmetry 1990, 1, 291.
75. b) Alvaro, G.; Savoia, D.; Valentinetti, M. R. Tetrahedron 1996, 52, 12571.
76. Hashimoto, Y.; Kobayashi, N.; Kai, A.; Saigo, K. Synlett 1995, 961.
77. Kawate, T.; Yamada, Hideki, Yamaguchi, K.; Nishida, A.; Nakagawa, M. Chem. Pharm. Bull. 1996, 44, 1776.
78. a) Laschat, S.; Kunz, H. Synlett 1990, 51.
79. b) Laschat, S.; Kunz, H. J. Org. Chem. 1991, 56, 5883.
80. a) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402.
81. b) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970.
82. Solladié-Cavallo, A.; Suffert, J.; Hanesslein, J.-L. Angew. Chem. 1980, 92, 1038; Angew. Chem., Int. Ed. Engl. 1980, 19, 1005.
83. Solladié-Cavallo, A.; Suffert, J.; Hanesslein, J.-L. Angew. Chem. 1980, 92, 1038; Angew. Chem., Int. Ed. Engl. 1980, 19, 1005.
84. Takemoto, Y.; Takeuchi, J.; Matsui, E.; Iwata, C. Chem. Pharm. Bull. 1996, 44, 948.
85. Alexakis, A.; Tranchier, J.-P.; Lensen, N.; Mangeney, P. J. Am. Chem. Soc. 1995, 117, 10768.
86. Matsubara, S.; Ukita, H.; Kodama, T.; Utimoto, K. Chem. Lett. 1994, 831.
87. Tsuchihashi, G. I.; Iriuchijam, S.; Maniwa, K. Tetrahedron Lett. 1973, 3389.
88. Ronan, B.; Marchalin, S.; Samuel, O.; Kagan, H. B. Tetrahedron Lett. 1988, 29, 6101.
89. a) Pyne, S. G.; Dikic, B. J. Chem. Soc., Chem. Commun. 1989, 826.
90. b) Pyne, S. G.; Dikic, B. J. Org. Chem. 1990, 55, 1932.
91. c) Pyne, S. G.; Chapman, S. L. J. Chem. Soc., Chem. Commun. 1986, 1688.
92. a) Fiaud, J.-C.; Kagan, H. B. Tetrahedron Lett. 1970, 1813.
93. b) Fiaud, J.-C.; Kagan, H. B. Tetrahedron Lett. 1971, 1019.
94. a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681.
95. b) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1991, 32, 3095.
96. c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron: Asymmetry 1993, 4, 1603.
97. d) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429.
98. e) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527.
99. a) Denmark, S. E.; Nakajima, N.; Nicaise, O. J. Am. Chem. Soc. 1994, 116, 8797.
100. b) Denmark, S. E.; Nakajima, N.; Nicaise, O.; Faucher, A.-M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884.
101. Jones, C. A.; Jones, I. G.; North, M.; Pool, C. R. Tetrahedron Lett. 1995, 36, 7885.
102. Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489.
103. a) Ermert, P.; Meyer, I.; Stucki, C.; Schneebeli, J.; Obrecht, J.-P. Tetrahedron Lett. 1988, 29, 1265.
104. b) Kober, R.; Steglich, W. Liebigs Ann. Chem. 1983, 599.
105. c) Kober, R.; Papadopoulos, K.; Miltz, W; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693.
106. d) Münster, P.; Steglich, W. Synthesis 1987, 223.
107. a) Hamon, D. P. G.; Razzino, P.; Massy-Westropp, R. A. J. Chem. Soc., Chem. Commun. 1991, 332.
108. b) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. J. Chem. Soc., Chem. Commun. 1991, 722.
109. c) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. Tetrahedron 1992, 48, 5163.
110. Katritzky, A. R.; Harris, P. A. Tetrahedron: Asymmetry 1992, 3, 437.
111. Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590.
112. a) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341.
113. b) Itsuno, S.; Sasaki, M.; Kuroda, S.; Ito, K. Tetrahedron: Asymmetry 1995, 6, 1531.
114. c) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem. 1997, 109, 105; Angew. Chem. Int. Ed. Engl. 1997, 36, 109.
115. c) Itsuno, S.; Watanabe, K.; Ito, K.; El-Shehawy, A. A.; Sarhan, A. A. Angew. Chem. 1997, 109, 105; Angew. Chem. Int. Ed. Engl. 1997, 36, 109.
116. a) Itsuno, S.; Hachisuka, C.; Kitano, K. Tetrahedron Lett. 1992, 33, 627.
117. b) Itsuno, S.; Hachisuka, C.; Ushijima, Y.; Ito, K. Synth. Commun. 1992, 22, 3229.
118. a) Itsuno, S.; Yanaka, H.; Hachisuka, C.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1991, 1341.
119. b) Itsuno, S.; Sasaki, M.; Kuroda, S.; Ito, K. Tetrahedron: Asymmetry 1995, 6, 1507.
120. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
121. a) Soai, K.; Hatanaka, M.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097.
122. b) Hayase, T.; Inoue, Y.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2509.
123. c) Suzuki, T.; Naarisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519.
124. d) Andersson, P. G.; Guijarro, D.; Tanner, D. Synlett 1996, 727.
125. Yang, T.-K.; Chen, R.-Y.; Lee, D.-S.; Peng, W.-S.; Jiang, Y.-Z.; Mi, A.-Q.; Jong, T.-T. J. Org. Chem. 1994, 59, 914.
126. Hua, D. H.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4.
127. Braun, M.; Opdenbusch, K. Angew. Chem. 1993, 105, 595; Angew. Chem., Int. Ed. Engl. 1993, 32, 578.
128. Braun, M.; Opdenbusch, K. Angew. Chem. 1993, 105, 595; Angew. Chem., Int. Ed. Engl. 1993, 32, 578.
129. a) Takahashi, H.; Tomita, K.; Otomasu, H. J. Chem. Soc., Chem. Commun. 1979, 668.
130. b) Takahashi, H.; Tomita, K.; Noguchi, H. Chem. Pharm. Bull. 1981, 39, 3387.
131. c) Takahashi, H.; Inagaki, H. Chem. Pharm. Bull. 1982, 30, 922.
132. d) Takahashi, H.; Suzuki, Y. Chem. Pharm. Bull. 1983, 31, 4295.
133. a) Enders, D. In Asymmetric Synthesis, Morrison, J. D., Ed.; Academic Press: Orlando, 1984, Vol. 3B; p. 275.
134. b) Enders, D.; Fey, P.; Kipphardt, H. Org. Synth.1987, 65, 173, 183.
135. c) Enders, D, Klatt, M. In Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A., Ed.; Wiley, New York, 1995, p. 178.
136. a) Enders, D.; Schubert, H.; Nübling, C. Angew. Chem. 1986, 98, 1118; Angew. Chem., Int. Ed. Engl. 1986, 25, 1109.
137. a) Enders, D.; Schubert, H.; Nübling, C. Angew. Chem. 1986, 98, 1118; Angew. Chem., Int. Ed. Engl. 1986, 25, 1109.
138. b) Enders, D.; Nübling, C.; Schubert, H. Liebigs Ann./Receuil, 1997, in press.
139. a) Denmark, S. E.; Weber, T.; Piotrowski, D. W. J. Am. Chem. Soc. 1987, 109, 2224.
140. b) Weber, T.; Edwards, J. P.; Denmark, S. E. Synlett 1989, 20.
141. c) Denmark, S. E.; Edwards, J. P.; Nicaise, O. J. Org. Chem. 1993, 58, 569.
142. a) Nübling, C.; Ph.D thesis, Aachen, 1987.
143. b) Denmark, S. E.; Nicaise, O.; Edwards, J. P. J. Org. Chem. 1990, 55, 6219.
144. Enders, D.; Bartzen, D. Liebigs Ann. Chem. 1991, 569.
145. Enders, D.; Tiebes, J. Liebigs Ann. Chem. 1993, 173.
146. a) Enders, D.; Funk, R.; Klatt, M.; Raabe, G.; Hovestreydt, E. R. Angew. Chem. 1993, 105, 418; Angew. Chem., Int. Ed. Engl. 1993, 32, 418.
147. a) Enders, D.; Funk, R.; Klatt, M.; Raabe, G.; Hovestreydt, E. R. Angew. Chem. 1993, 105, 418; Angew. Chem., Int. Ed. Engl. 1993, 32, 418.
148. b) Enders, D.; Klatt, M.; Funk, R. Synlett 1993, 226.
149. Denmark, S. E.; Nicaise, O. Synlett 1993, 359.
150. Enders, D.; Schankat, J.; Klatt, M. Synlett 1994, 795.
151. Yanagisawa, A.; Ogasawara, K.; Yasue, K; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1996, 367.
152. a) Enders, D.; Reinhold, U. Angew. Chem. 1995, 107, 1332; Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
153. a) Enders, D.; Reinhold, U. Angew. Chem. 1995, 107, 1332; Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
154. b) Enders, D.; Reinhold, U. Liebigs Ann. 1996, 11.
155. c) Enders, D.; Reinhold, U. Synlett 1994, 792.
156. Enders, D.; Chelain, E.; Raabe, G. Bull. Soc. Chim. Fr. 1997, in press.
157. a) Enders, D.; Lochtman, R.; Raabe, G. Synlett 1996, 126.
158. b) Enders, D.; Lochtman, R. Synlett 1997, 355.
159. Enders, D.; Meiers, M. Angew. Chem. 1996, 108, 2391; Angew. Chem., Int. Ed. Engl. 1996, 35, 2261.
160. Enders, D.; Meiers, M. Angew. Chem. 1996, 108, 2391; Angew. Chem., Int. Ed. Engl. 1996, 35, 2261.
161. Kim, Y. H.; Choi, J. Y. Tetrahedron Lett. 1996, 37, 5543.
162. a) Thiam, M.; Chastrette, F. Tetrahedron Lett. 1990, 31, 1429.
163. b) Thiam, M.; Chastrette, F. Bull. Soc. Chim. Fr. 1992, 129, 161.
164. c) Thiam, M.; Slassi, A.; Chastrette, F. Synth. Commun. 1992, 31, 83.
165. a) Alexakis, A.; Lensen, N.; Mangeney, P. Tetrahedron Lett. 1991, 32, 1171.
166. b) Alexakis, A.; Lensen, N.; Mangeney, P. Synlett 1991, 625.
167. c) Alexakis, A.; Lensen, N.; Tranchier, J.-P.; Mangeney, P. J. Org. Chem. 1992, 57, 4565.
168. d) Alexakis, A.; Mangeney, P.; Lensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure & Appl. Chem. 1996, 68, 531.
169. a) Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron Lett. 1987, 25, 4973.
170. b) Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1988, 44, 5440.
171. Dieter, R. K.; Datar, R. Can. J. Chem. 1993, 71, 814.
172. a) Gallagher, P. T.; Lightfoot, A. P.; Moody, C. J.; Slawin, A. M. Z. Synlett 1995, 445.
173. b) Brown, D. S.; Gallagher, P. T.; Lightfoot, A. P.; Moody, C. J.; Slawin A. M. Z.; Swann, E. Tetrahedron 1995, 51, 11473.
174. c) Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. J. Org. Chem. 1997, 62, 746.
175. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415.
176. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5273.
177. Fujioka, H.; Masahiro, M.; Okaichi, Y.; Yoshida, T. Annoura, H.; Kita, Y.; Tamura, Y. Chem. Pharm. Bull. 1989, 37, 602 and literature cited therein.
178. Ukaji, Y.; Kume, K.; Watai, T.; Fujisawa, T. Chem. Lett. 1991, 173.
179. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997.
180. a) Chang, Z.-Y.; Coates, R. M. J. Org. Chem. 1990, 55, 3475.
181. b) Chang, Z.-Y.; Coates, R. M. J. Org. Chem. 1990, 55, 3464.
182. Rohloff, J. C.; Alfredson, T. V.; Schwartz, M. A. Tetrahedron Lett. 1994, 35, 1011.
183. Annunziata, R.; Cinquini, M. Synthesis 1992, 929.
184. a) Murahashi, S.-I.; Sun J.; Tsuda, T. Tetrahedron Lett. 1993, 34, 2645.
185. b) Murahashi, S.-I. Angew. Chem. 1995, 107, 2670; Angew. Chem., Int. Ed. Engl. 1995, 34, 2443.
186. b) Murahashi, S.-I. Angew. Chem. 1995, 107, 2670; Angew. Chem., Int. Ed. Engl. 1995, 34, 2443.
187. a) Ukaji, Y.; Hatanaka, T.; Ahmed, A.; Inomata, K. Chem. Lett. 1993, 1313.
188. b) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53.
189. c) Ukaji, Y.; Shimizu, Y.; Kenmoku, Y.; Ahmed, A.; Inomata, K. Chem. Lett. 1997, 59.
190. Richter-Addo, G. B.; Knight, D. A.; Dewey, M. A.; Arif, A. M.; Gladysz J. Am. Chem. Soc. 1993, 115, 11863.
191. Stark, G. A.; Arif, A. M.; Gladysz, J. A. Organometallics 1994, 13, 4523.