Construction of heterocycles by the strategic use of alkyne π-activation in catalyzed cascade reactions

Synthesis

Volumn , Issue 20, 2008, Pages 3183-3204

  Kirsch, Stefan F ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cascade reactions; Catalysis; Gold; Heterocycles; Platinum

Indexed keywords

ACETYLENE; ACIDS; CARBONYLATION; CARBOXYLATION; CYCLIZATION; ESTERIFICATION; ESTERS; NITROGEN COMPOUNDS; NUCLEOPHILES; ORGANIC COMPOUNDS; PLATINUM;

CASCADE REACTIONS; CYCLIZATION REACTIONS; CYCLOISOMERIZATIONS; FUNCTIONALIZATION; HETEROCYCLES; INTRAMOLECULAR ADDITIONS; LEWIS ACIDS; MISCELLANEOUS REACTIONS; SYNTHESIS OF;

ADDITION REACTIONS;

ALKYNE; AMINE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; IMINE;

ADDITION REACTION; CARBOXYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; CYCLOADDITION; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; SYNTHESIS;

EID: 55349083675     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083164     Document Type: Review

References (287)

1. For recent reviews, see: (a) Tietze, L. F. Chem. Rev. 1996, 96, 115.
2. (b) Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. 1993, 32, 131.
3. (c) Tietze, L. F.; Lieb, M. Curr. Opin. Chem. Biol. 1998, 2, 363.
4. (d) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304.
5. (e) Tietze, L. F.; Brasche, G.; Gericke, G. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
6. (f) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem. Int. Ed. 2006, 45, 7134.
7. (g) Pellisier, H. Tetrahedron 2006, 62, 2143.
8. (a) Robinson, R. J. Chem. Soc. 1917, 111, 762.
9. (b) Schöpf, C.; Lehmann, G.; Arnold, W. Angew. Chem. 1937, 50, 779.
10. (a) D'Souza, D. M.; Müller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095.
11. (b) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
12. (c) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
13. (d) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101.
14. (e) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076.
15. (a) Fürstner, A.; Davies, P. W. Angew. Chem. Int. Ed. 2007, 46, 3410.
16. (b) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
17. (c) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
18. (d) Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem. Int. Ed. 2006, 45, 7896.
19. (e) Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
20. (f) Arcadi, A.; Di Guiseppe, S. Curr. Org. Chem. 2004, 8, 795.
21. (g) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts 2003, 16, 397.
22. (h) Hashmi, A. S. K. Angew. Chem. Int. Ed. 2005, 44, 6990.
23. (i) Hashmi, A. S. K. Catal. Today 2007, 122, 211.
24. (j) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
25. (k) Dyker, G. Angew. Chem. Int. Ed. 2000, 39, 4237.
26. (l) Muzart, J. Tetrahedron 2008, 64, 5815.
27. (m) Shen, H. C. Tetrahedron 2008, 64, 3885. For a recent review on coinage metals in heterocycle synthesis, see:
28. (n) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395.
29. For selected applications in total synthesis, see: (a) Fursmer, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
30. (b) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801.
31. (c) Simmons, E. M.; Sarpong, R. Org. Lett. 2006, 8, 2883.
32. (d) Fürstner, A.; Kennedy, J. W. J. Chem. Eur. J. 2006, 12, 7398.
33. (e) Linghu, X.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem. Int. Ed. 2007, 46, 7671.
34. (f) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
35. For a review on the reactivity of propargylic esters, see: (a) Marion, N.; Nolan, S. P. Angew. Chem. Int. Ed. 2007, 46, 2750.
36. (b) Marco-Contelles, J.; Soriano, E. Chem. Eur. J. 2007, 13, 1350. For a review on the cycloisomerization of enynes, see:
37. (c) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271.
38. (d) Nieto-Oberhuber, C.; López, S.; Jiménez- Núñez, E.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 5916.
39. (e) Ma, S.; Yu, S.; Gu, Z. Angew. Chem. Int. Ed. 2006, 45, 200.
40. (f) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813. For a review on the hydroamination of alkynes, see:
41. (g) Widenhoefer,R. A.; Han, X. Eur. J. Org. Chem. 2006, 4555. For a review on the reactions of oxo-alkynes, see:
42. (h) Patil, N. T.; Yamamoto, Y. ARKIVOC 2007, (v), 6. For a review on 1,2-alkyl migrations, see:
43. (i) Brone, B.; Kirsch, S. F. Chem. Eur. J. 2008, 14, 3514. For a review on stereoselective catalysis, see:
44. (j) Bongers, N.; Krause, N. Angew. Chem. Int. Ed. 2008, 47, 2178. For a review on C-H activation, see:
45. (k) Skouta, R.; Li, C.-J. Tetrahedron 2008, 64, 4917.
46. For a review, see: Hoffmann-Röder, A.; Krause, N. Org. Biomol. Chem. 2005, 3, 387.
47. For selected examples, see: (a) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700.
48. (b) Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798.
49. (c) Kerber, W. D.; Gagné, M. R. Org. Lett. 2005, 7, 3379.
50. For a review, see: Nevado, C.; Echavarren, A. M. Synthesis 2005, 167.
51. For leading examples, see: (a) Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485.
52. (b) Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669.
53. (c) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
54. (d) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913.
55. (e) Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
56. (f) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055.
57. (g) Nevado, C.; Echavarren, A. M. Chem. Eur. J. 2005, 11, 3155.
58. Hashmi, A. S. K.; Blanco, M. C. Eur. J. Org. Chem. 2006, 4340.
59. Hashmi, A. S. K.; Blanco, M. C.; Kurpejovic, E.; Frey, W.; Bats, J. W. Adv. Synth. Catal. 2006, 348, 709.
60. (a) Ferrer, C.; Amijs, C. H. M.; Echavarren, A. M. Chem. Eur. J. 2007, 13, 1358.
61. (b) Ferrer, C.; Echavarren, A. M. Angew. Chem. Int. Ed. 2006, 45, 1105.
62. (c) Bhuvaneswari, S.; Jeganmohan, M.; Cheng, C.-H. Chem. Eur. J. 2007, 13, 8285.
63. Harrison, T. J.; Patrick, B. O.; Dake, G. R. Org. Lett. 2007, 9, 367.
64. (a) Hotha, S.; Kashyap, S. J. Am. Chem. Soc. 2006, 128, 9620.
65. (b) Kashyap, S.; Hotha, S. Tetrahedron Lett. 2006, 47, 2021.
66. (c) Kashyap, S.; Vidadala, S. R.; Hotha, S. Tetrahedron Lett. 2007, 48, 8960.
67. (d) Sureshkumar, G.; Hotha, S. Tetrahedron Lett. 2007, 48, 6564.
68. (a) Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729.
69. (b) Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem. Int. Ed. 2002, 41, 4563.
70. (a) Jung, H. H.; Floreancig, P. E. J. Org. Chem. 2007, 72, 7359.
71. (b) Jung, H. H.; Floreancig, P. E. Org. Lett. 2006, 8, 1949.
72. For leading references, see: (a) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem. Int. Ed. 1998, 37, 1415.
73. (b) Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409.
74. (c) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem. Int. Ed. 2000, 39, 2285.
75. (a) Antoniotti, S.; Genin, E.; Michelet, V.; Genêt, J.-P. J. Am. Chem. Soc. 2005, 127, 9976.
76. (b) Li, Y.; Zhou, F.; Forsyth, C. J. Angew. Chem. Int. Ed. 2007, 46, 279.
77. (a) Belting, V.; Krause, N. Org. Lett. 2006, 8, 4489.
78. (b) Liu, B.; De Brabander, J. K. Org. Lett. 2006, 8, 4907.
79. (c) Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191.
80. (d) Diéguez-Vázquez, A.; Tzschucke, C. C.; Lam, W. Y.; Ley, S. V. Angew. Chem. Int. Ed. 2008, 47, 209.
81. (e) Zhang, Y.; Xue, J.; Xin, Z.; Xie, Z.; Li, Y. Synlett 2008, 940.
82. Tian, G.-Q.; Shi, M. Org. Lett. 2007, 9, 4917.
83. Liu, Y.; Song, F.; Guo, S. J. Am. Chem. Soc. 2006, 128, 11332.
84. (a) Barluenga, J.; Diéguez, A.; Fernández, A.; Rodríguez, F.; Fañanás, F. J. Angew. Chem. Int. Ed. 2006, 45, 2091.
85. (b) Barluenga, J.; Fernández, A.; Satrústegui, A.; Diéguez, A.; Rodríguez, F.; Fañanás, F. J. Chem. Eur. J. 2008, 14, 4153.
86. Yang, T.; Campbell, L.; Dixon, D. J. J. Am. Chem. Soc. 2007, 129, 12070.
87. For leading references, see: (a) Arcadi, A.; Bianchi, G.; Marinelli, F. Synthesis 2004, 610.
88. (b) Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799.
89. (c) Fukuda, Y.; Utimoto, K. Synthesis 1991, 975.
90. Alfonsi, M.; Arcadi, A.; Aschi, M.; Bianchi, G.; Marinelli, F. J. Org. Chem. 2005, 70, 2265.
91. Zhang, Y.; Donahue, J. P.; Li, C.-J. Org. Lett. 2007, 9, 627.
92. Kamijo, S.; Yamamoto, Y. J. Org. Chem. 2003, 68, 4764.
93. (a) Mizushima, E.; Hayashi, T.; Tanaka, M. Org. Lett. 2003, 5, 3349.
94. (b) Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297.
95. Liu, X.-Y.; Ding, P.; Huang, J.-S.; Che, C.-M. Org. Lett. 2007, 9, 2645.
96. Luo, Y.; Li, Z.; Li, C.-J. Org. Lett. 2005, 7, 2675.
97. Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
98. Witham, C. A.; Mauleón, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
99. Kimball, D. B.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572.
100. (a) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785.
101. (b) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863.
102. For a related palladium-catalyzed process, see: Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
103. Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024.
104. (a) Fürstner, A.; Aïssa, C. J. Am. Chem. Soc. 2006, 128, 6306.
105. (b) Fürstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244.
106. Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022.
107. Nakamura, I.; Chan, C. S.; Araki, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2008, 10, 309.
108. Fürstner, A.; Heilmann, E. K.; Davies, P. W. Angew. Chem. Int. Ed. 2007, 46, 4760.
109. For a related palladium-catalyzed process, see: (a) Balme, G.; Bouyssi, D.; Lomberget, T.; Monteiro, N. Synthesis 2003, 2115.
110. (b) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001.
111. Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546.
112. Nakamura, I.; Yamagishi, U.; Song, D.; Konta, S.; Yamamoto, Y. Angew. Chem. Int. Ed. 2007, 46, 2284.
113. (a) Istrate, F. M.; Gagosz, F. Org. Lett. 2007, 9, 3181.
114. (b) Cariou, K.; Ronan, B.; Mignani, S.; Fensterbank, L.; Malacria, M. Angew. Chem. Int. Ed. 2007, 46, 1881.
115. Li, G.; Huang, X.; Zhang, L. Angew. Chem. Int. Ed. 2008, 47, 346.
116. Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem. Int. Ed. 2006, 45, 4473.
117. Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2007, 9, 4081.
118. (a) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
119. (b) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921.
120. (c) Asao, N.; Sato, K.; Meggenbateer; Yamamoto, Y. J. Org. Chem. 2005, 70, 3682.
121. (d) Hildebrandt, D.; Hüggenberg, W.; Kanthak, M.; Plöger, T.; Müller, I. M.; Dyker, G. Chem. Commun. 2006, 2260.
122. (e) Dyker, G.; Hildebrandt, D. J. Org. Chem. 2005, 70, 6093.
123. (f) Sato, K.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2005, 70, 8977.
124. (g) Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458.
125. (h) Asao, N.; Aikawa, H. J. Org. Chem. 2006, 71, 5249.
126. (i) Asao, N.; Sato, K. Org. Lett. 2006, 8, 5361.
127. (j) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605.
128. For a theoretical calculation, see: Straub, B. Chem. Commun. 2004, 1726.
129. For an alternative pathway, see: Kim, N.; Kim, Y.; Park, W.; Sung, D.; Gupta, A. K.; Oh, C. H. Org. Lett. 2005, 7, 5289.
130. Dyker, G.; Hildebrandt, D.; Liu, J.; Merz, K. Angew. Chem. Int. Ed. 2003, 42, 4399.
131. Zhu, J.; Germain, A. R.; Porco, J. A. Jr. Angew. Chem. Int. Ed. 2004, 43, 1239.
132. Asao, N.; Sato, K.; Yamamoto, Y. Tetrahedron Lett. 2003, 44, 5675.
133. Su, S.; Porco, J. A. Jr. J. Am. Chem. Soc. 2007, 129, 7744.
134. Kusama, H.; Miyashita, Y.; Takaya, J.; Iwasawa, N. Org. Lett. 2006, 8, 289.
135. Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260.
136. (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
137. (b) Patil, N. T.; Yamamoto, Y. J. Org. Chem. 2004, 69, 5139.
138. (c) Nakamura, H.; Ohtaka, M.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 7631.
139. (d) Asao, N.; Chan, C. S.; Takahashi, K.; Yamamoto, Y. Tetrahedron 2005, 61, 11322.
140. (e) Wei, L.-L.; Wei, L.-M.; Pan, W.-B.; Wu, M.-J. Synlett 2004, 1497.
141. (f) Godet, T.; Vaxelaire, C.; Michel, C.; Milet, A.; Belmont, P. Chem. Eur. J. 2007, 13, 5632.
142. Patil, N. T.; Pahadi, N. K.; Yamamoto, Y. J. Org. Chem. 2005, 70, 10096.
143. Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953.
144. Asao, N.; Yudha, S.; Nogami, T.; Yamamoto, Y. Angew. Chem. Int. Ed. 2005, 44, 5526.
145. For further reactions of alkynylimines, see: (a) Rubin, M.; Dromek, A.; Gevorgyan, V. Synlett 2003, 2265.
146. (b) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980.
147. (c) Dai, G.; Larock, R. C. J. Org. Chem. 2003, 68, 920.
148. (d) Yanada, R.; Obika, S.; Kono, H.; Takemoto, Y. Angew. Chem. Int. Ed. 2006, 45, 3822.
149. (a) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164.
150. (b) Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679.
151. Patil, N. T.; Wu, H.; Yamamoto, Y. J. Org. Chem. 2005, 70, 4531.
152. (a) Liu, X.; Pan, Z.; Shu, X.; Duan, X.; Liang, Y. Synlett 2006, 1962.
153. (b) Oh, C. H.; Reddy, V. R.; Kim, A.; Rhim, C. Y. Tetrahedron Lett. 2006, 47, 5307.
154. (c) Gulias, M.; Rodriguez, J. R.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2003, 5, 1975.
155. (a) Zhang, J.; Schmalz, H.-G. Angew. Chem. Int. Ed. 2006, 45, 6704.
156. (b) Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814.
157. Liu, Y.; Liu, M.; Guo, S.; Tu, H.; Gao, H. Org. Lett. 2006, 8, 3445.
158. Xiao, Y.; Zhang, J. Angew. Chem. Int. Ed. 2008, 47, 1903.
159. For Pd(II) and Pd(0) catalysts, see, inter alia: (a) Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295.
160. (b) Hashmi, A. S. K. Angew. Chem. Int. Ed. 1995, 34, 1581. For Ag(I) and Rh(I) catalysts, see, inter alia:
161. (c) Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 59, 7169.
162. (d) Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 960. For Au catalysts, see, inter alia:
163. (e) Zhou, C.-Y.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2006, 8, 325.
164. (f) Ref. 18c.
165. (g) Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432. For Hg(II) catalysts, see, inter alia:
166. (h) Imagawa, H.; Kurisaki, T.; Nishizawa, M. Org. Lett. 2004, 6, 3679.
167. (a) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y. T.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
168. (b) Ref. 3e.
169. (c) Brown, R. C. D. Angew. Chem. Int. Ed. 2005, 44, 850.
170. (a) Kirsch, S. F.; Binder, J. T.; Liébert, C.; Menz, H. Angew. Chem. Int. Ed. 2006, 45, 5878.
171. (b) For a related study, see: Bunelle, E. M.; Smith, C. R.; Lee, S. K.; Singaram, W. S.; Rhodes, A. J.; Sarpong, R. Tetrahedron 2008, 64, 7008.
172. Crone, B.; Kirsch, S. F. J. Org. Chem. 2007, 72, 5435.
173. Binder, J. T.; Crone, B.; Kirsch, S. F.; Liébert, C.; Menz, H. Eur. J. Org. Chem. 2007, 1636.
174. Smith, C. R.; Bunnelle, E. M.; Rhodes, A. J.; Sarpong, R. Org. Lett. 2007, 9, 1169.
175. For a related cyclization, see: (a) Seregin, I. V.; Gevorgyan, V. J. Am. Chem. Soc. 2006, 128, 12050.
176. (b) Seregin, I. V.; Schammel, A. W.; Gevorgyan, V. Org. Lett. 2007, 9, 3433.
177. (a) Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391.
178. (b) Hashmi, A. S. K.; Rudolph, M.; Schymura, S.; Visus, J.; Frey, W. Eur. J. Org. Chem. 2006, 4905.
179. (c) Kang, J.-E.; Kim, H.-B.; Lee, J.-W.; Shin, S. Org. Lett. 2006, 8, 3537.
180. (d) Milton, M. D.; Inada, Y.; Nishibayashi, Y.; Uemura, S. Chem. Commun. 2004, 2712.
181. (a) Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515.
182. (b) Kang, J.-E.; Shin, S. Synlett 2006, 111.
183. (a) Robles-Machín, R.; Adrio, J.; Carretero, J. C. J. Org. Chem. 2006, 71, 5023.
184. (b) Buzas, A.; Gagosz, F. Synlett 2006, 2727.
185. (c) Ritter, S.; Horino, Y.; Lex, J.; Schmalz, H.-G. Synlett 2006, 3309.
186. (a) Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763.
187. (b) Istrate, F. M.; Buzas, A. K.; Jurberg, I. D.; Odabachian, Y.; Gagosz, F. Org. Lett. 2008, 10, 925.
188. Yamamoto, H.; Pandey, G.; Asai, Y.; Nakano, M.; Kinoshita, A.; Namba, K.; Imagawa, H.; Nishizawa, M. Org. Lett. 2007, 9, 4029.
189. For leading examples, see: (a) Nishizawa, M.; Takenaka, H.; Hirotsu, K.; Higuchi, T.; Hayashi, Y. J. Am. Chem. Soc. 1984, 106, 4290.
190. (b) Imagawa, H.; Asai, Y.; Takano, H.; Hamagaki, H.; Nishizawa, M. Org. Lett. 2006, 8, 447.
191. (c) Imagawa, H.; Fujikawa, Y.; Tsuchihiro, Y.; Kinoshita, A.; Yoshinaga, T.; Takao, H.; Nishizawa, M. Synlett 2006, 639.
192. Asao, N.; Aikawa, H.; Tago, S.; Umetsu, K. Org. Lett. 2007, 9, 4299.
193. Pujanauski, B. G.; Prasad, B. A. B.; Sarpong, R. J. Am. Chem. Soc. 2006, 128, 6786.
194. Motamed, M.; Bunnelle, E. M.; Singaram, S. W.; Sarpong, R. Org. Lett. 2007, 9, 2167.
195. Hardin, A. R.; Sarpong, R. Org. Lett. 2007, 9, 4547.
196. Davies, P. W.; Albrecht, J.-C. Chem. Commun. 2008, 238.
197. Buzas, A.; Istrate, F.; Gagosz, F. Org. Lett. 2006, 8, 1957.
198. Yeom, H.-S.; Yoon, S.-J.; Shin, S. Tetrahedron Lett. 2007, 48, 4817.
199. Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804.
200. Zhang, G.; Catalano, V. J.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 11358.
201. Luo, T.; Schreiber, S. L. Angew. Chem. Int. Ed. 2007, 46, 8250.
202. (a) Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel'in, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440. For pyrroles, see:
203. (b) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
204. (c) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697. For furans, see:
205. (d) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95.
206. (e) Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500.
207. (f) Dudnik, A. S.; Gevorgyan, V. Angew. Chem. Int. Ed. 2007, 46, 5195.
208. Schwier, T.; Sromek, A. W.; Yap, D. M. L.; Chernyak, D.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 9868.
209. Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem. Int. Ed. 2004, 43, 2280.
210. (a) Ref. 5a.
211. (b) Ref. 35a.
212. (c) Ref. 35b.
213. (d) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 2402.
214. (e) Nieto-Oberhuber, C.; López, S.; Muñoz, M. P.; Cárdenas, D. J.; Buñuel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem. Int. Ed. 2005, 44, 6146.
215. Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc, 2001, 123, 10511.
216. (a) Blum, J.; Beer-Kraft, H.; Badrieh, Y. J. Org. Chem. 1995, 60, 5567.
217. (b) Ref. 95b-d.
218. (c) Nevado, C.; Ferrer, C.; Echavarren, A. M. Org. Lett. 2004, 6, 3191.
219. (d) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
220. (e) Nieto-Oberhuber, C.; López, S.; Muñoz, M. P.; Jiménez-Núñez, E.; Cárdenas, C.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 1694.
221. (f) Nieto-Oberhuber, C.; Perez-Galan, P.; Herrero-Gómez, E.; Lauterbach, T.; Rodriguez, C.; López, S.; Bour, C.; Rosellon, A.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269.
222. For a theoretical study, see: Soriano, E.; Ballesteros, P.; Marco-Contelles, J. J. Org. Chem. 2004, 69, 8018.
223. (a) Méndez, M.; Muñoz, M. P.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 11549.
224. (b) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627.
225. (c) Nieto-Oberhuber, C.; Muñoz, M. P.; López, S.; Jiménez-Núñez, E.; Nevado, C.; Herrero-Gómez, E.; Raducan, M.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 1677.
226. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genet, J.-P. Chem. Commun. 2004, 850.
227. (e) Muñoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293.
228. (f) Muñoz, M. P.; Méndez, M.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Synthesis 2003, 2898.
229. (g) Toullec, P. Y.; Genin, E.; Leseurre, L.; Genêt, J.-P. Angew. Chem. Int. Ed. 2006, 45, 7427.
230. (h) Leseurre, L.; Toullec, P. Y.; Genêt, J.-P.; Michelet, V. Org. Lett. 2007, 9, 4049.
231. (i) Genin, E.; Leseurre, L.; Toullec, P. Y.; Genêt, J.-P.; Michelet, V. Synlett 2007, 1780.
232. (j) Kim, S. M.; Park, J. H.; Choi, S. Y.; Chung, Y. K. Angew. Chem. Int. Ed. 2007, 46, 6172.
233. (k) Amijs, C. H. M.; Ferrer, C.; Echavarren, A. M. Chem. Commun, 2007, 698.
234. (l) Ferrer, C.; Raducan, M.; Nevado, C.; Claverie, C. K.; Echavarren, A. M. Tetrahedron 2007, 63, 6306.
235. (a) Matsuda, T.; Kadowaki, S.; Goya, T.; Murakami, M. Synlett 2006, 575.
236. (b) Luzung, M. R.; Mauleón, P.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12402.
237. (a) Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509.
238. (b) Marion, F.; Coulomb, J.; Servais, A.; Courillon, C.; Fensterbank, L.; Malacria, M. Tetrahedron 2006, 62, 3856.
239. Couty, S.; Meyer, C.; Cossy, J. Angew. Chem. Int. Ed. 2006, 45, 6726.
240. Jiménez-Núñez, E.; Claverie, C. K.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem. Int. Ed. 2006, 45, 5452.
241. Schelwies, M.; Dempwolff, A. L.; Rominger, F.; Helmchen, G. Angew. Chem. Int. Ed. 2007, 46, 5598.
242. For leading examples, see: (a) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
243. (b) Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858.
244. (c) Fehr, C.; Farris, I.; Sommer, H. Org. Lett. 2006, 8, 1839.
245. (d) Sun, J.; Conley, M. P.; Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2006, 128, 9705.
246. (e) Gagosz, F. Org. Lett. 2005, 7, 4129.
247. (f) Kirsch, S. F.; Binder, J. T.; Crone, B.; Duschek, A.; Haug, T. T.; Liébert, C.; Menz, H. Angew. Chem. Int. Ed. 2007, 46, 2310.
248. (g) Buzas, A. K.; Istrate, F. M.; Gagosz, F. Angew. Chem. Int. Ed. 2007, 46, 1141.
249. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
250. Lim, C.; Kang, J.-E.; Lee, J.-E.; Shin, S. Org. Lett. 2007, 9, 3539.
251. Horino, Y.; Luzung, M. R.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 11364.
252. Sherry, B. D.; Maus, L.; Laforteza, B. N.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 8132.
253. (a) Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978.
254. (b) Grissom, J. W.; Kilingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603.
255. Overman, L. E. Angew. Chem. Int. Ed. 1984, 23, 579.
256. Suhre, M. H.; Reif, M.; Kirsch, S. F. Org. Lett. 2005, 7, 3925.
257. Binder, J. T.; Kirsch, S. F. Org. Lett. 2006, 8, 2151.
258. Menz, H.; Kirsch, S. F. Org. Lett. 2006, 8, 4795.
259. (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553.
260. (b) Martin-Matute, B.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem. Int. Ed. 2001, 40, 4754.
261. (a) Hashmi, A. S. K.; Salathé, R.; Frey, W. Chem. Eur. J. 2006, 12, 6991.
262. (b) Hashmi, A. S. K.; Wölfie, M.; Ata, F.; Hamzic, M.; Salathé, R.; Frey, W. Adv. Synth. Catal. 2006, 348, 2501.
263. (c) Hashmi, A. S. K.; Weyrauch, J. P.; Rudolph, M.; Kuperjovic, E. Angew. Chem. Int. Ed 2004, 43, 6546.
264. (d) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Org. Lett. 2001, 3, 3769.
265. (e) Hashmi, A. S. K.; Weyrauch, J. P.; Kuperjovic, E.; Frost, T. M.; Miehlich, B.; Frey, W.; Bats, J. W. Chem. Eur. J. 2006, 12, 5806.
266. (f) Hashmi, A. S. K.; Haufe, P.; Schmid, C.; Nass, A. R.; Frey, W. Chem. Eur. J. 2006, 12, 5376.
267. (a) Hashmi, A. S. K.; Rudolph, M.; Weyrauch, J. P.; Wölfie, M.; Frey, W.; Bats, J. W. Angew. Chem. Int. Ed. 2005, 44, 2798.
268. (b) Hashmi, A. S. K.; Kurpejovic, E.; Wölfie, M.; Frey, W.; Bats, J. W. Adv. Synth. Catal. 2007, 349, 1743.
269. (a) Arcadi, A.; Di Giuseppe, S.; Marinelli, F.; Rossi, E. Adv. Synth. Catal. 2001, 343, 443.
270. (b) Arcadi, A.; Di Giuseppe, S.; Marinelli, F.; Rossi, E. Tetrahedron: Asymmetry 2001, 12, 2715.
271. (c) Arcadi, A.; Chiarini, M.; Di Giuseppe, S.; Marinelli, F. Synlett 2003, 203.
272. Harrison, T. J.; Kozak, J. A.; Corbella-Pané, M.; Dake, G. R. J. Org. Chem. 2006, 71, 4525.
273. Abbiati, B.; Arcadi, A.; Bianchi, G.; Di Giuseppe, S.; Marinelli, F.; Rossi, E. J. Org. Chem. 2003, 68, 6959.
274. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
275. Yan, B.; Liu, Y. Org. Lett. 2007, 9, 4323.
276. Ding, Q.; Wu, J. Org. Lett. 2007, 9, 4959.
277. For another combination of π-activation and enamine catalysis, see: Binder, J. T.; Crone, B.; Haug, T. T.; Menz, H. Org. Lett. 2008, 10, 1025.
278. (a) Skouta, R.; Li, C.-J. Angew. Chem. Int. Ed. 2007, 46, 1117.
279. (b) Skouta, R.; Li, C.-J. Tetrahedron Lett. 2007, 48, 8343.
280. Skouta, R.; Li, C.-J. Synlett 2007, 1759.
281. Hashmi, A. S. K.; Schäfer, S.; Wölfle, M.; Gil, C. D.; Fischer, P.; Laguna, A.; Blanco, M. C.; Gimeno, M. C. Angew. Chem. Int. Ed. 2007, 46, 6184.
282. (a) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 4160.
283. (b) Li, G.; Zhang, L. Angew. Chem. Int. Ed. 2007, 46, 5156.
284. Gasparrini, F.; Giovannoli, M.; Misiti, D.; Natile, G.; Palmieri, G.; Maresca, L. J. Am. Chem. Soc. 1993, 115, 4401.
285. Shu, X.-Z.; Liu, X.-Y.; Xiao, H.-Q.; Ji, K.-G.; Guo, L.-N.; Liang, Y.-M. Adv. Synth. Catal. 2008, 350, 243.
286. Fukudome, Y.; Naito, H.; Hata, T.; Urabe, H. J. Am. Chem. Soc. 2008, 130, 1820.
287. Barluenga, J.; Fernández-Rodríguez, M. A.; García-García, P.; Aguilar, E. J. Am. Chem. Soc. 2008, 130, 2764.