Unsaturated nitriles: Conjugate additions of carbon nucleophiles to a recalcitrant class of acceptors

Chemical Reviews

Volumn 103, Issue 5, 2003, Pages 2035-2077

  Fleming, Fraser F ^a   Wang, Qunzhao ^a  

^a DUQUESNE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AGENTS; CHEMICAL ACTIVATION; COMPOSITION EFFECTS; COPPER COMPOUNDS; FREE RADICAL REACTIONS; NITROGEN COMPOUNDS; ZINC; ZINC COMPOUNDS;

CARBANIONS; CARBON NUCLEOPHILES; CONJUGATE ADDITIONS; ESTER ENOLATES; ORGANOMETALLIC ADDITIONS; RECALCITRANT CLASS; UNSATURATED NITRILES;

UNSATURATED COMPOUNDS;

EID: 0038661129     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr020045d     Document Type: Article

References (312)

1. Perlmutter, P. In Conjugate Addition Reactions in Organic Synthesis; Pergamon: New York, 1992; Chapter 1.
2. Hulce, M.; Chapdelaine, M. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I.; Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 237-268
3. (b) Taylor, R. J. K. Synthesis 1985, 364.
4. Perlmutter, P. In Conjugate Addition Reactions in Organic Synthesis; Pergamon: New York, 1992; Chapter 4.
5. (a) House, H. O. Acc. Chem. Res. 1976, 9, 59.
6. (a) House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 3893.
7. (b) Yoneda, R.; Harusawa, S.; Kurihara, T. J. Chem. Soc., Perkin Trans. 1. 1988, 3163.
8. (d) Totleben, M. J.; Curran, D. P.; Wipf, P. J. Org. Chem. 1992, 57, 1740.
9. Bergmann, E. D.; Ginsburg, D.; Pappo, R. Organic React. 1959, 10, 179.
10. Conjugate additions to doubly activated alkylidenemalononitriles, and related congeners, are distinctly different, reflecting the high reactivity imparted by substituting and olefin with two electron withdrawing groups. Alkenenitriles containing additional activating groups are therefore not surveyed and the reader is directed to an excellent leading reference: Wallenfels, K.; Friedrich, K,; Reiser, J.; Ertel, W.; Thieme, H. K. Angew. Chem., Int. Ed. Engl. 1976, 15, 261.
11. Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597.
12. Kohler, E. P. J. Am. Chem. Soc. 1906, 35, R 486.
13. Brown, J. M.; Armstrong, S. K. In Comprehensive Organometallic Chemistry: A review of the Literature 1982-1994; Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 11, Chapter 3.
14. Phenylacetonitrile carbanion is stabilized more by the phenyl group than by the nitrile: Bradamante, S.; Pagani, G. A. J. Chem. Soc., Perkin Trans. 2 1986, 1035.
15. Blechert, S.; Wirth, T. Tetrahedron Lett. 1991, 32, 7237.
16. Kulp, S. S.; DiConcetto, J. A. J. Chem. Educ. 1990, 67, 271.
17. Hauser, C. R.; Humphlett, W. J. J. Org. Chem. 1950, 15, 359.
18. Eicher, T.; Böhm, S. Chem. Ber. 1974, 107, 2186.
19. Ramart-Lucas, Compte Rendus 1912, 155, 39.
20. Wawzonek, S. J. Am. Chem. Soc. 1946, 68, 1157.
21. (a) Maxim, N.; Aldea, G. Bull. Soc. Chim. Fr. 1935, 2, 582.
22. (b) Mazim, N.; Aldea, G. Bull. Soc. Chim. Fr. 1936, 3, 1329.
23. Wawzonek, S. J. Am. Chem. Soc. 1951, 73, 5746.
24. Burckhalter, J. H.; Kurath, P. J. Am. Chem. Soc. 1959, 81, 395.
25. Sindelar, K.; Holubek, J.; Ryska, M.; Svatek, E.; Urban, J.; Grimova, J.; Cervena, I.; Hrubantova, M.; Protiva, M. Collect. Czech. Chem. Commun. 1983, 48, 1187.
26. Wang, S.-H.; Zhu, Y.-Q. Acta Chim. Sinica 1982, 40, 267.
27. Fleming, F. F.; Wang, Q.; Steward, O. W. Org. Lett. 2000, 2, 1477.
28. Fleming, F. F.; Wang, Q.; Zhang, Z.; Steward, O. W. J. Org. Chem. 2002, 67, 5953.
29. Kingsbury, C. A. J. Org. Chem. 1968, 33, 1128.
30. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
31. The cyclization most likely involves an alkyllithium intermediate rather than radical cyclization stereochemistries differ from those of radical cyclizations: Bailey, W. F.; Carson, M. W. J. Org. Chem. 1998, 63, 361.
32. Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 4353.
33. Walters, E. A.; Long, F. A. J. Am. Chem. Soc. 1969, 91, 3733.
34. Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
35. Woodward, S. Chem. Soc. Rev. 2000, 29, 393.
36. 4b Krause, N.; Wagner, R.; Gerold, A. J. Am. Chem. Soc. 1994, 116, 381.
37. a's of nitriles, see: (a) Colominas, C.; Orozco, M.; Luque, F. J.; Borrell, J. I.; Teixido, J. J. Org. Chem. 1998, 63, 4947.
38. For Lewis acidity, see: Gridnev, I. D.; Gridnev, N. A. Russ. Chem. Rev. 1995, 64, 1091.
39. (a) Lipshutz, B. H.; Crow, R.; Dimock, S. H.; Ellsworth, E. L.; Smith, R. A. J.; Behling, J. R. J. Am. Chem. Soc. 1990, 112, 4063.
40. (b) Lipshutz, B. H.; Hackmann, C. J. Org. Chem. 1994, 59, 7437.
41. Wipf, P.; Venkatraman, S. J. Org. Chem. 1993, 58, 3455.
42. Dieter, P.; Venkatraman, S. J. Org. Chem. 2000, 65, 8715.
43. (b) Jones, P.; Knochel, P. J. Chem. Soc., Perkin Trans. 1 1997, 3117.
44. Quendo, A.; Rousseau, G. Synth. Commun. 1989, 19, 1551.
45. Kogen, H.; Tomioka, K.; Hashimoto, S.; Koga, K. Tetrahedron 1981, 37, 3951.
46. Weiberth, F. J.; Hall, S. S. J. Org. Chem. 1987, 52, 3901.
47. (a) Majetich, G.; Casares, A.; Chapman, D.; Behnke, M. Tetrahedron Lett. 1983, 24, 1909.
48. (b) Majetich, G.; Casares, A.; Chapman, D.; Behnke, M. J. Org. Chem. 1986, 51, 1745.
49. Fang, J. M.; Chang, H. T. J. Chem. Soc., Perkin Trans. 1 1988, 1945.
50. Yoneda, R.; Inagaki, N.; Harusawa, S.; Kurhara, T. Chem. Pharm. Bull. 1992, 40, 21.
51. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. J. Org. Chem. 1984, 49, 9, 3938.
52. Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047.
53. Barbero, A.; Blanco, Y.; Pulido, F. J. Chem. Commun. 2001, 1606.
54. Miyaura, N.; Itoh, M.; Suzuki, A. Tetrahedron Lett. 1976, 255.
55. (a) Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1978, 100, 3240.
56. (b) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119.
57. Pews, R. G.; Gall, J. A. J. Org. Chem. 1994, 59, 6783.
58. Villemin, D.; Sauvaget, F.; Hajek, M. Tetrahedron Lett. 1994, 35, 3537.
59. Huff, R.; Mutterer, F.; Weiss, C. D. Helv. Chim. Acta 1977, 60, 907.
60. Sato, K.; Tamura, M.; Tamoto, K.; Omote, M.; Ando, A.; Kumadaki, I. Chem. Pharm. Bull. 2000, 48, 1023.
61. Martin, P.; Steiner, E.; Streith, J.; Winkler, T.; Bellus, D. Tetrahedron 1985, 41, 4057.
62. Sengmany, S.; Leonel, E.; Paugam, J. P.; Nedelec, J.-Y. Synthesis 2002, 533.
63. (a) Ryu, I.; Kusano, K.; Yamazaki, H.; Sonoda, N. J. Org. Chem. 1991, 56, 5003.
64. (b) Thoma, G.; Giese, B. Tetrahedron Lett. 1989, 30, 2907.
65. (c) Pike P.; Hershberger, S.; Hershberger, J. Tetrahedron 1988, 44, 6295.
66. (a) Childs, R. F.; Mulholland, D. L.; Nixon, A. Can J. Chem. 1982, 60, 801.
67. (b) Beattie, I. R.; Jones, P. J. Angew Chem., Int. Ed. Engl. 1996, 35, 1527.
68. Asscher, M.; Vofsi, D. J. Chem. Soc. B 1968, 947.
69. (a) Shono, T.; Ishifune, M.; Ishige, O.; Uyama, H.; Kashimura, S. Tetrahedron Lett. 1990, 31, 7181.
70. Nerdel, F.; Brodowski, W.; Buddrus, J.; Fligge, M.; Weyerstahl, P.; Ulm, K.; Finger, C.; Klamann, D. Chem. Ber. 1968, 101, 1407.
71. Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589.
72. (a) Crandall, J. K.; Ayers, T. A. Organometallics 1992, 11, 473.
73. (b) Blanchard, P.; Da Silva, A. D.; Fourrey, J.-L.; Machado, A. S.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 8069.
74. (a) Nii, S.; Terao, J.; Kambe, N. J. Org. Chem. 2000, 65, 5291.
75. (b) Maillard, B.; Forrest, D.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 7024.
76. Tsunoi, S.; Ryu, I.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Synlett 1995, 1249.
77. Takai, K.; Ueda, T.; Ikeda, N.; Moriwake, T. J. Org. Chem. 1996, 61, 7990.
78. Orsini, F. Synthesis 1985, 500.
79. Blanchard, P.; Da Silva, A. D.; El Kortbi, M. S.; Fourney, J. L.; Robert-Gero, M. J. Org. Chem. 1993, 58, 6517
80. Reddy, C. K.; Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1996, 37, 4495.
81. Jones, P.; Knochel, P. J. Chem. Soc., Perkin Trans. 1 1997, 3117.
82. Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.-F. Synlett 1993, 266.
83. Frantz, D. E.; Singleton, D. A. J. Am. Chem. Soc. 2000, 122, 3288.
84. Dupuy, C.; Petrier, C.; Sarandeses, L. A.; Luche, J. L. Synth. Commun. 1991, 21, 643.
85. Blanchard, P.; El Korbti, M. S.; Fourrey, J.-L.; Robert-Gero, M. Tetrahedron Lett. 1992, 33, 3319.
86. Sarandeses, L. A.; Mourino, A.; Luche, J.-L. J. Chem. Soc., Chem. Commun. 1992, 798.
87. Shono, T.; Nishiguchi, I.; Sasaki, M. J. Am. Chem. Soc. 1978, 100, 4314.
88. Inaba, S.; Matsumoto, H.; Rieke, R. D. J. Org. Chem. 1984, 49, 2093.
89. Lebedev, S. A.; Lopatina, V. S.; Petrov, E. S. Zh. Obschch. Khim. 1995, 65, 501.
90. Sustmann, R.; Hopp, P.; Holl, P. Tetraheron Lett. 1989, 30, 689.
91. Cannes, C.; Condon, S.; Durandetti, M.; Perichon, J.; Nedelec, J.-Y. J. Org. Chem. 2000, 65, 4575.
92. Hashimoto, I.; Tsuruta, N.; Ryang, M.; Tsutsumi, S. J. Org. Chem. 1970, 35, 3748.
93. Readman, S. K.; Marsden, S. P.; Hodgson, A. Synlett 2000, 1628.
94. Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418.
95. Condon-Gueugnot, S.; Leonel, E.; Nedelec, J.-Y.; Perichon, J. J. Org. Chem. 1995, 60, 7684.
96. Condon-Gueugnot, S.; Dupre, D.; Nedelec, J.-Y.; Perichon, J. Synthesis 1997, 1457.
97. Inaba, S.-C.; Rieke, R. D. J. Org. Chem. 1985, 50, 1373.
98. Yanagi, T.; Sasaki, H.; Suzuki, A.; Miyaura, N. Synth. Commun. 1996, 26, 2503.
99. Sim, T. B.; Choi, J.; Joung, M. J.; Yoon, N. M. J. Org. Chem. 1997, 62, 2357.
100. Perez, I.; Sestelo, J. P.; Maestro, M. A.; Mourino, A.; Sarandeses, L. A. J. Org. Chem. 1998, 63, 10074.
101. Kochi, J. K.; Davis, D. D. J. Am. Chem. Soc. 1964, 86, 5264.
102. 3SnH the formation of a chromated nitrile is avoided: Narasaka, K.; Sakurai, H. Chem. Lett. 1993, 1269.
103. Fuchibe, K.; Iwasawa, N. Org. Lett. 2000, 2, 3297.
104. Kasattkin, A. N.; Tsypyshev, O. Yu.; Romanova, T. Yu.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 1154.
105. Cambie, R. C.; Metzler, M. R.; Rutledge, P. S.; Woodgate, P. D. J. Organomet. Chem. 1990, 381, C26.
106. Depree, G. J.; Main, L.; Nocholson, B. K. J. Organomet. Chem. 1998, 551, 281.
107. Tashtoush, H. I.; Sustmann, R. Chem. Ber. 1992, 125, 287.
108. Zhi, C.; Chen, Q.-Y. J. Chem. Soc., Perkin Trans. 1 1996, 1741.
109. Sakurai, H.; Narasaka, K. Chem. Lett. 1994, 2017.
110. a of acetonitrile being recently revised upward to ∼30. (a) Bordwell, F. G.; Matthews, W. S. J. Am. Chem. Soc. 1974, 96, 1214.
111. (b) Richard, J. P.; Williams, G.; Gao, J. J. Am. Chem. Soc. 1999, 121, 715.
112. (a) Lucius, R.; Loos, R.; Mayr, H. Angew. Chem., Int. Ed. Engl. 2002, 41, 92.
113. (b) Lucius, R.; Mayr, H. Angew. Chem., Int. Ed. Engl. 2000, 39, 1995.
114. Akuamoah, R. K.; Brown, P. E.; Marcus, W. Y.; Steele, J. E. J. Chem. Soc., Perkin Trans. 1 1995, 197.
115. Hoshino, O.; Sawaki, S.; Shimamura, N.; Onodera, A.; Umezawa, B. Chem. Pharm. Bull. 1987, 35, 2734.
116. Pasquinet, E.; Rocca, P.; Richalot, S.; Gueritte, F.; Guenard, D.; Godard, A.; Marsais, F.; Queguiner, G. J. Org. Chem. 2001, 66, 2654.
117. Hegarty, P.; Mann, J. Synlett. 1993, 553.
118. Rigo, B.; Kolocouris, N. J. Heterocyclic Chem. 1983, 20, 893.
119. (a) Ghosh, A.; Bhattacharya, S.; Chatterjee, A. Indian. J. Chem. B 1990, 29, 203.
120. (b) Bhattacharya, S.; Mandal, A. N.; Chaudhuri, S. R. R.; Chatterjee, A. J. Chem. Soc., Perkin Trans. 1 1984, 5.
121. Berlin, K. D, Morgan, J. G.; Durham, N. N.; Chesnut, R. W. J. Org. Chem. 1971, 36, 1599.
122. Kraus, G. A.; Sy, J. O. J. Org. Chem. 1989, 54, 77.
123. Giasuddin Ahmed, M.; Iqbal Moeiz, S. M.; Asghari Ahmed, S.; Kiuchi, F.; Tsuda, Y. Tetrahedron 2001, 57, 3143.
124. Heathcock, C. H.; Norman, M. H.; Dickman, D. A. J. Org. Chem. 1990, 55, 798.
125. Epstein, W. W.; Grua, J. R.; Gregonis, D. J. Org. Chem. 1982, 47, 1128.
126. Down, G. J. Aust. J. Chem. 1982, 35, 1269.
127. (a) Quinkert, G.; Müller, T.; Königer, A.; Schultheis, O.; Sickenberger, B.; Dürner, G. Tetrahedron Lett. 1992, 33, 3469.
128. (b) Quinkert, G.; Schmalz, H.-G.; Walzer, E.; Gross, S.; Kowalczyk-Przewloka, T.; Schierloh, C.; Dürner, G.; Bats, J. W.; Kessler, H. Liebigs. Ann. Chem. 1988, 283.
129. Cameron, R.; Nicholson, S. H.; Robinson, D. H.; Suckling, C. J.; Wood, H. S. C. J. Chem. Soc., Perkin Trans. 1 1985, 2133.
130. Hwu, J. R.; Hakimelahi, G. H.; Chou, C.-T. Tetrahedron Lett 1992, 33, 6469.
131. Cartier, D.; Levy, J. Tetrahedron 1990, 46, 5295.
132. Cooke, E.; Paradellis, T. C.; Edward, J. T. Can. J. Chem. 1982, 60, 29.
133. Katritzky, A. R.; Wang, J.; Henderson, S. A. Heterocycles 1998, 48, 1567.
134. Lu, L.; Shoemaker, R. K.; Wheeler, D. M. S. Tetrahedron Lett. 1989, 30, 6993.
135. Boyer, J.; Corriu, R. J. P.; Perz, R.; Reye, C. Tetrahedron 1983, 39, 117.
136. Forrester, A. R.; Irikawa, H.; Thomson, R. H.; Woo, S. O.; King, T. J. J. Chem. Soc., Perkin Trans. 1 1981, 1712.
137. Bergmann, E. D.; Szmuszkovicz, J. J. Am. Chem. Soc. 1953, 75, 3226.
138. Brattesani, D. N.; Heathcock, C. H. J. Org. Chem. 1975, 40, 2165.
139. Mann, J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. A., Eds.; Pergamon Press, New York, 1991; Vol. 3, Chapter 3.7, p 839.
140. (a) Boss, A. M.; Clissold, D. W.; Mann, J.; Markson, A. J.; Thickitt, C. P. Tetrahedron 1989, 45, 6011.
141. (b) McCague, R.; Jarman, M.; Rowlands, M. G.; Mann, J.; Thickitt, C. P.; Clissold, D. W.; Neidle, S.; Webster, G. J. Chem. Soc., Perkin Trans. 1 1989, 196.
142. (a) Bremner, D. H.; Ringan, N. S. J. Chem. Soc., Perkin Trans. 1. 1991, 1265.
143. (b) Bremner, D. H.; Campbell, M. M. J. Chem. Soc., Perkin Trans 1 1977, 2298.
144. Gonzalez, J.; Sanchez, F.; Torres, T. Synthesis 1983, 911.
145. Dryanska, V. Synth. Commun. 1985, 15, 899.
146. Rice, J. E.; Shih, H. C.; Hussain, N.; LaVoie, E. J. J. Org. Chem. 1987, 52, 849.
147. Chen, C.; Liao, Y.; Huang, Y.-Z. Tetrahedron 1989, 45, 3011.
148. McCoy, L. L. J. Org. Chem. 1960, 25, 2078.
149. Ahlbrecht, H.; Dietz, M. Synthesis 1985, 417.
150. For an overview of nitrile anion structure see: Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 66, 1.
151. Nitriles are powerful inductive stabilizing groups with weak delocalizing effects: (a) Bradamante, S.; Pagini, G. A. J. Chem. Soc., Perkin Trans. 2 1986, 1035.
152. (b) Van Wijnen, W. T.; Steinberg, H.; De Boer, T. J. Tetrahedron 1972, 28, 5423.
153. (c) Dayal, S. K.; Ehrenson, S.; Taft, R. W. J. Am. Chem. Soc. 1972, 94, 9113.
154. Bernasconi, C. F.; Zitomer, J. L.; Fox, J. P.; Howard, K. A. J. Org. Chem. 1984, 49, 482.
155. Albright, J. D. Tetrahedron 1983, 39, 3207.
156. (a) Desos, P.; Schlewer, G.; Wermuth, C. G. Heterocycles 1989, 28, 1085.
157. (b) Sircar, I.; Bobowski, G.; Bristol, J. A.; Weishaar, R. E.; Evans, D. B. J. Med. Chem. 1986, 29, 261.
158. (c) Sircar, I.; Duel, B. L.; Bobowski, G.; Bristol, J. A.; Evans, D. B. J. Med. Chem. 1985, 28, 1405.
159. (a) Kraus, G. A.; Dneprovskaia, E. Tetrahedron Lett. 2000, 41, 21.
160. (b) Miyashita, A.; Numata, A.; Suzuki, Y.; Iwamoto, K.; Higashino, T. Chem. Lett. 1997, 697.
161. (c) Miyashita, A.; Matsuoka, Y.; Numata, A.; Higashino, T. Chem. Pharm. Bull. 1996, 44, 448.
162. (d) Bridge, A. W.; Fenton, G.; Halley, F.; Hursthouse, M. B.; Lehmann, C. W.; Lythgoe, D. J. J. Chem. Soc., Perkin Trans. 1 1993, 2761.
163. (e) Higashino, T.; Kokubo, H.; Hayashi, E. Chem. Pharm. Bull. 1985, 33, 950.
164. (f) Welter, W.; Hüttelmaier, T.; Matterstock, K.; Mildenberger, H. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1982, 37B, 923.
165. Ho, T. L. In Tandem Organic Reactions. Wiley: New York, 1992.
166. Ahlbrecht, H.; Ibe, M. Synthesis 1985, 421.
167. Jonczyk, A.; Golinski, M.; Winiarski, J. Liebigs Ann. Chem. 1989, 203.
168. Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
169. Kugita, H.; Oine, T. Chem. Pharm. Bull. 1963, 11, 253.
170. Joshi, U. R.; Samant, S. D. Indian J. Chem. B 1990, 29B, 22.
171. Hoffmann, K.; Kebrle, J.; Schmid, H. J. Helv. Chim. Acta 1957, 40, 387.
172. Hartmann, R. W.; Batzl, C. J. Med. Chem. 1986, 29, 1362.
173. Leung, C.-S.; Rowlands, M. G.; Jarman, M.; Foster, A. B.; Griggs, L. J.; Wilman, D. E. V. J. Med. Chem. 1987, 30, 1550.
174. Binet du Jassonneix, C. Bull. Chem. Soc. Fr. 1975, 758.
175. Al-Arab, M. M.; Tabba, H. D.; Abu-Yousef, I. A.; Olmstead, M. M. Tetrahedron 1988, 44, 7293.
176. Alberola, A.; Alonso, F.; Cuadrado, P.; Carmen Sanudo, M. Gazz. Chim. Ital. 1987, 117, 461.
177. (a) Mukherjee, A.; Seth, M.; Bhaduri, A. P.; Singh, S.; Chatterjee, R. K. Indian J. Chem. B 1990, 29, 191.
178. (b) Kaddah, A. M.; Khalil, A. M.; Tawfik, N. I. Indian J. Chem. B 1980, 19, 122.
179. Fadda, A. A.; Refat, H. M. Synth. Commun. 2000, 30, 341.
180. Kisanga, P.; D'Sa, B.; Verkade, J. J. Org. Chem. 1998, 63, 10057.
181. Tinant, B.; Wu, S.; Declercq, J.-P.; Van Meerssche, M.; Masamba, W.; De Mesmaeker, A.; Viehe, H. G. J. Chem. Soc., Perkin Trans. 2 1988, 1045.
182. Nath, M.; Srivastava, P.; Goel, A.; Ram, V. J. Eur. J. Org. Chem. 1998, 2083.
183. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
184. Kitayama, T. Tetrahedron 1996, 52, 6139.
185. Newkome, G. R.; Moorefield, C. N.; Theriot, K. J. J. Org. Chem. 1988, 53, 3, 5552.
186. Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226.
187. Lee, W. Y.; Jang., S. Y.; Chae, W. K.; Park, O. S. Synth. Commun. 1993, 23, 3037.
188. Newkome, G. R.; Weis, C. D. J. Org. Chem. 1991, 56, 4798.
189. (a) Sanchez, I. H.; Lopez, F. J.; Soria, J. J.; Larraza, M. I.; Flores, H. J. J. Am. Chem. Soc. 1983, 105, 7640.
190. (b) Sanchez, I. H.; Soria, J. J.; Lopez, F. J.; Larraza, M. I.; Flores, H. J. J. Org. Chem. 1984, 49, 157.
191. Nagao, Y.; Kaneko, K.; Fujita, E. Tetrahedron Lett. 1976, 1215.
192. Zschiesche, R.; Reissig, H.-U. Liebigs Ann. Chem. 1988, 1165.
193. Nakamura, K.; Kitayama, T.; Inoue, Y.; Ohno, A. Bull. Chem. Soc. Jpn. 1990, 63, 91.
194. (a) Takeuchi, Y.; Nagata, K.; Koizumi, T. J. Org. Chem. 1989, 54, 5453.
195. (b) Takeuchi, Y.; Nagata, K.; Koizumi, T. J. Org. Chem. 1987, 52, 5061.
196. Ono, N.; Hamamoto, I.; Kamimura, A.; Kaji, A.; Tamura, R. Synthesis 1987, 258.
197. Takechi, H.; Machida, M. Synthesis 1989, 206.
198. Baasner, B.; Marhold, A.; Negele, M. J. Fluorine Chem. 1990, 46, 161.
199. Ono, N.; Kamimura, A.; Miyake, H.; Hamamoto, I.; Kaji, A. J. Org. Chem. 1985, 50, 3692.
200. Ballini, R.; Bosica, G. Eur. J. Org. Chem. 1998, 355, 5.
201. Ballini, R.; Marziali, P.; Mozzicafreddo, A. J. Org. Chem. 1996, 61, 3209.
202. Garg, N.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1993, 49, 5189.
203. Jonczyk, A.; Radwan-Pytlewski, T. Pol. J. Chem. 1995, 69, 1161.
204. Hanack, M.; Auchter, A.; Wunde, C.; Stoll, T. Liebigs Ann. Chem. 1989, 853.
205. Kaiser, C.; Trost, B. M.; Beeson, J.; Weinstock, J. J. Org. Chem. 1965, 30, 3972.
206. Makosza, M.; Krylova, I. Liebigs Ann./Recueil 1997, 2337.
207. Sodoyer, R.; Abad, E.; Rouvier, E.; Cambon, A. J. Fluorine Chem. 1983, 22, 401.
208. Ueno, Y.; Ohta, M.; Okawara, M. J. J. Organometallic Chem. 1980, 197, C1.
209. Sanchez, I. H.; Aguilar, M. A. Synthesis 1981, 55.
210. Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655.
211. Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215
212. Evans, D. A.; Bilodeau, M. T.; Somers, T. C.; Clardy, J.; Cherry, D.; Kato, Y. J. Org. Chem. 1991, 56, 5750.
213. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc., Perkin Trans. 1 1987, 717.
214. Baumann, M. E.; Bosshard, H.; Breitenstein, W.; Rist, G. Helv. Chim. Acta 1986, 69, 396.
215. Nikitin, K. V.; Andryukhova, N. P. Mendeleev Commun. 1999, 168.
216. Kraus, G. A.; Sugimoto, H. Synthetic Commun. 1977, 7, 505.
217. Dryanska, V.; Popandova-Yambolieva, K.; Ivanov, C. Tetrahedron Lett. 1979, 443.
218. Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819.
219. Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V.; Wang, M.; Kolb, H. J. Org. Chem. 2000, 65, 8819.
220. Katritzky, A. R.; Voronkov, M. V.; Toader, D. J. Org. Chem. 1998, 63, 9987.
221. Shono, T.; Kashimura, S.; Yamaguchi, Y.; Kuwata, F. Tetrahedron Lett. 1987, 28, 4411.
222. Rautenstrauch, V.; Ohloff, G. Helv. Chim. Acta 1971, 54, 1776.
223. Barker, J. M.; Huddleston, P. R.; Smith, R. J. Chem. Res. (S), 1994, 16.
224. Bram, G.; Sansoulet, J.; Galons, H.; Bensaid, Y.; Combet-Farnoux, C.; Miocque, M. Tetrahedron Lett. 1985, 26, 4601.
225. Hashimoto, S.; Matsumoto, K.; Otani, S.; Hayami, J.; Yoshida, H. Synthesis 1984, 164.
226. Brisse, F.; Durocher, G.; Gauthier, S.; Gravel, D.; Marques, R.; Vergelati, C.; Zelent, B. J. Am. Chem. Soc. 1986, 108, 6579.
227. Chang, H.-F.; Cho, B. P. J. Org. Chem. 1999, 64, 9051.
228. Basha, F. Z.; DeBernardis, J. F.; Spanton, S. J. Org. Chem. 1985, 50, 4160.
229. Flemming, F. F.; Hussain, Z.; Weaver, D.; Norman, R. E. J. Org. Chem. 1997, 62, 1305.
230. (a) Lambs, L.; Singh, N. P.; Biellmann, J.-F. Tetrahedron Lett. 1991, 32, 2637.
231. (b) Lambs, L.; Singh, N. P.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 6301.
232. (a) Ahlbrecht, H.; Pfaff, K. Synthesis 1978, 897.
233. (b) Ahlbrecht, H.; Ibe, M. Synthesis 1988, 210.
234. Ye, S.; Huang, Z.-Z.; Xia, C.-A.; Tang, Y.; Dai, L.-X. J. Am. Chem. Soc. 2002, 124, 2432.
235. Kempf, B.; Hampel, N.; Ofial, A. R.; Mayr, H. Chem. Eur. J., in press.
236. (a) Posner, G. H.; Oh, C. H.; Gerena, L.; Milhouse, W. K. J. Med. Chem. 1992, 35, 2459.
237. (c) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz., J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207.
238. (d) Mandell, L.; Piper, J. U.; Singh, K. P. J. Org. Chem. 1963, 28, 3440.
239. Fleming, I.; Harley-Mason, J. J. Chem. Soc. 1964, 2165.
240. Brannock, K. C.; Bell, A.; Burpitt, R. D.; Kelly, C. A. J. Org. Chem. 1964, 29, 801.
241. Ahmed, M. G.; Ahmed, S. A.; Hickmott, P. W. J. Chem. Soc., Perkin Trans. 1 1980, 2383.
242. Hammadi, M.; Villemin, D. Synth. Commun. 1996, 26, 2901.
243. Corriu, R. J. P.; Huynh, V.; Moreau, J. J. E. J. Organomet. Chem. 1983, 259, 283.
244. Allin, S. M.; Button, M. A. C.; Shuttleworth, S. J. Synlett 1997, 725.
245. Fourtinon, M.; De Jeso, B.; Pommier, J.-C. J. Organomet. Chem. 1985, 289, 239.
246. Cai, B.; Pan, Y,; Dewan, J. C.; Wink, D. J.; Murphy, R. B.; Schuster, D. I. Tetrahedron Lett. 1993, 34, 2067.
247. Mandell, L.; Singh, K. P. J. Am. Chem. Soc. 1961, 83, 1766.
248. Jones, R. C. F.; Hirst, S. C. Tetrahedron Lett. 1989, 30, 5361.
249. Tokumitsu, T. Bull. Chem. Soc. Jpn. 1990, 63, 1921.
250. Guerret, P.; Langlois, M. J. Heterocyclic Chem. 1979, 16, 1163.
251. Bischoff, C.; Schröder, E.; Gründemann, E. J. Prakt. Chem. 1984, 326, 849.
252. Nagarajan, K.; Rao, V. R.; Shah, R. K.; Shenoy, S. J.; Fritz, H.; Richter, W. J.; Muller, D. Helv. Chim. Acta 1988, 71, 77.
253. Abbas, R.; Willette, R. E.; Edwards, J. M. J. Pharm. Sci. 1977, 66, 1583.
254. Rozantsev, E. G.; Dagonneau, M.; Kagan, E. S.; Mikhailov, V. I.; Sholle, V. D. J. Chem. Res. (S) 1979, 2901.
255. Hickmott, P. W.; Jutle, K. K.; Pienar, D. H. J. Chem. Soc., Perkin Trans. 1 1990, 2399.
256. Szabo, L.; Kalaus G.; Kalman, A.; Kolonits, P.; Szantay, C. Heterocycles 1995, 40, 155.
257. Kobor, J.; Sohar, P.; Fulop, F. Tetrahedron 1994, 50, 4873.
258. Majchrzak, M. W.; Simchen, G. Synthesis 1986, 956.
259. Murahashi, S.-I.; Sasao, S.; Saito, E.; Naota, T. Tetrahedron 1993, 39, 8805.
260. (a) Yamada, S.-I.; Hiroi, K.; Achiwa, K. Tetrahedron Lett. 1969, 4233.
261. (b) Hiroi, K.; Achiwa, K.; Yamada, S.-I. Chem. Pharm. Bull. 1972, 20, 246.
262. O'Neill, P. M.; Miller, A.; Bickley, J. F.; Scheinmann, F.; Oh, C. H.; Posner, G. H. Tetrahedron Lett. 1999, 40, 9133.
263. Keller, L.; Camara, C.; Pinheiro, A.; Dumas, F.; d'Angelo, J. Tetrahedron Lett. 2001, 42, 381.
264. Gaidarova, E. L.; Grishina, V. G. Synlett 1992, 89.
265. De Jeso, B.; Pommier, J.-C. Tetrahedron Lett. 1980, 21, 4511.
266. De Jeso, B.; Pommier, J.-C. J. Chem. Soc., Chem. Commun. 1977, 565.
267. Rodriguez, J. G.; Urrutia, A. J. Heterocyclic Chem. 1999, 36, 129.
268. Dryanska, V.; Ivanov, C. Synthesis 1980, 317.
269. Liu, H.-J.; Shia, K.-S.; Shang, X.; Zhu, B.-Y. Tetrahedron 1999, 55, 3803.
270. Rosenblum, M.; Turnbull, M.; Begum, M. K. J. Organomet. Chem. 1987, 321, 67.
271. Cooke, M. P., Jr.; Parlman, R. M. J. Am. Chem. Soc. 1977, 99, 5222.
272. Giese, B.; Thoma, G. Helv. Chim. Acta 1991, 74, 1143.
273. Soderberg B. C.; York, D. C.; Hoyle, T. R.; Rehberg, G. M.; Suriano, J. A. Organometallics 1994, 13, 4501.
274. Ohno, T.; Sakai, M.; Ishino, Y.; Shibata, T.; Maekawa, H.; Nishiguchi, I. Org. Lett. 2001, 3, 3439.
275. Yasuda, M.; Ohigashi, N.; Baba, A. Chem. Lett. 2000, 1266.
276. Mathew, A. E.; Dodd, J. R. J. Heterocyclic Chem. 1985, 22, 225.
277. Houghton, R. P.; Shervington, L. A. J. Chem. Res. 1989, 239.
278. Somawardhana, C. W.; Sajjad, M.; Lambrecht, R. M. J. Chem. Soc., Chem. Commun. 1990, 370.
279. Kawasaki, Y.; Fujii, A.; Nakano, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1999, 64, 4214.
280. Kim, S.; Lee, P. H. Tetrahedron Lett. 1988, 29, 5413.
281. Abdou, W. M.; Ganoub, N. A. F.; Shaddy, A. A. M. Tetrahedron 1998, 54, 9079.
282. Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 4, 667.
283. Hagiwara, H.; Eda, Y.; Morohashi, K.; Suzuki, T.; Ando, M.; Ito, N. Tetrahedron Lett. 1998, 39, 4055.
284. Moreno-Manas, M.; Pleixats, R.; Roglans, A. Synlett 1997, 1157.
285. Larock, R. C.; Yum, E. K.; Yang, H. Tetrahedron 1994, 50, 305.
286. Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079.
287. Huang, Q.; Larock, R. C. Org. Lett. 2002, 4, 2505.
288. Lautens, M.; Paquin, J.-F.; Piguel, S.; Dahlamnn, M. J. Org. Chem. 2001, 66, 8127.
289. Eggers, K.; Fyles, T. M.; Montoya-Pelaez, P. J. J. Org. Chem. 2001, 66, 2966.
290. Pereyre, M.; Colin, G.; Valade, J. C. R. Hebd. Seances Acad. Sci., Ser. C 1967, 264, 1204.
291. Ali, S. M.; Rousseau, G. Tetrahedron 1990, 46, 7011.
292. Boularand, G.; Vessiere, R. Bull. Soc. Chim. Fr. 1967, 1706.
293. Westmijze, H.; Kleijn, H.; Vermeer, P. Synthesis. 1978, 454.
294. Corey, E. J.; Tramontano, A. J. Am. Chem. Soc. 1984, 106, 462.
295. Kleijn, H.; Westmijze, H.; Meijer, J.; Vermeer, P. J. Organomet. Chem. 1981, 206, 257.
296. Bennani, Y. L. J. Org. Chem. 1996, 61, 3542.
297. Westmijze, H.; Kleijn, H.; Vermeer, P. Tetrahedron Lett. 1979, 3327.
298. Etienne, M.; Guerchais, J. E. J. Chem. Soc., Dalton Trans. 1989, 2187.
299. Fleming, F. F.; Dudipati, V.; Stewart, O. W. Organic Lett. 2002, 4, 659.
300. Reddy, G. S.; Mandell, L.; Goldstein, J. H. J. Am. Chem. Soc. 1961, 83, 1300.
301. Creary, X. Chem. Rev. 1991, 91, 1625.
302. The calculations were performed using the Gaussian 98, Hatree-Fock, 6-31G basis set. The results are qualitatively the same as those for acrolein (Fleming, I. In Frontier Orbitals and Organic Reaction; Wiley: London, 1976) and acrylonitrile
303. (Valenciano, J.; Cuadro, A. M.; Vaquero, J. J.; Alvarez-Builla, J.; Palmeiro, R.; Castano, O. J. Org. Chem. 1999, 64, 9001).
304. (a) Tucker, C. E.; Majid, T. N.; Knochel, P. J. Am. Chem. Soc. 1992, 114, 3983.
305. (b) Parham, W. E.; Jones, L. D. J. Org. Chem. 1976, 41, 1187.
306. (a) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333.
307. (b) Lee, J.-s.; Velarde-Ortiz, R.; Guijarro, A.; Wurst, J. R.; Rieke, R. D. J. Org. Chem. 2000, 65, 5428.
308. (c) Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618.
309. (d) Thibonnet, J.; Knochel, P. Tetrahedron Lett. 2000, 41, 3319.
310. (e) Kitagawa, K.; Inoue, A.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. Engl. 2000, 39, 2481.
311. (f) Burns, T. P.; Rieke, R. D. J. Org. Chem. 1987, 52, 3674.
312. Krief, A. Tetrahedron 1980, 36, 2531.