Copper-catalyzed asymmetric alkylation of imines with dialkylzinc and related reactions

Chemical Reviews

Volumn 108, Issue 8, 2008, Pages 2874-2886

  Yamada, Ken Ichi ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; CHEMICAL REACTIONS; HYDROCARBONS;

ALKYNYLATION; ASYMMETRIC ALKYLATION; ASYMMETRIC ALLYLATION; DIALKYL ZINC REAGENTS;

NITROGEN COMPOUNDS;

AMINE; COPPER; IMINE; LIGAND; ORGANOMETALLIC COMPOUND; ZINC;

ALKYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; REVIEW; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; AMINES; CATALYSIS; COPPER; IMINES; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 51049097914     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr078370u     Document Type: Review

References (245)

1. Reviews for addition to C=N controlled by chiral auxiliary: (a) Friestad, G. K. Eur. J. Org. Chem. 2005, 3157.
2. (b) Zhou, P.; Chen, B.; Davis, F. A. Tetrahedron 2004, 60, 8003.
3. (c) Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253.
4. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
5. (e) Alvaro, G.; Savoia, D. Synlett 2002, 651.
6. (f) Bloch, R. Chem. Rev. 1998, 98, 1407.
7. (g) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
8. (h) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
9. (a) Tomioka, K. Synthesis 1990, 541.
10. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
11. (c) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999.
12. (d) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315.
13. (e) Iguchi, M.; Yamada, K.; Tomioka, K. In Organolithiums in Enantioselective Synthesis; Hodgson, D. M., Ed.; Springer, Berlin, 2003; p 22.
14. (a) Takahashi, H.; Suzuki, Y.; Inagaki, H. Chem. Pharm. Bull. 1982, 30, 3160.
15. (b) Takahashi, H.; Chida, Y.; Suzuki, T.; Yanaura, S.; Suzuki, Y.; Masuda, C. Chem. Pharm. Bull. 1983, 31, 1659.
16. (c) Takahashi, H.; Suzuki, Y.; Hori, T. Chem. Pharm. Bull. 1983, 31, 2183.
17. (d) Suzuki, Y.; Takahashi, H. Chem. Pharm. Bull. 1983, 31, 2895.
18. (e) Takahashi, H.; Chida, Y.; Yoshii, T.; Suzuki, T.; Yanaura, S. Chem. Pharm. Bull. 1986, 34, 12071.
19. (a) Wu, M.-J.; Pridgen, L. N. Synlett 1990, 636.
20. (b) Wu, M.-J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340.
21. (c) Pridgen, L. D.; Mokhallalati, M. K.; Wu, M.-J. J. Org. Chem. 1992, 57, 1237.
22. (d) Mokhallalati, M. K.; Pridgen, L. N. Synth. Commun. 1993, 23, 2055.
23. (e) Muralidharan, K. R.; Mokhallalati, M. K.; Pridgen, L. N. Tetrahedron Lett. 1994, 35, 7489.
24. (f) Pridgen, L. D.; Mokhallalati, M. K.; McGuire, M. A. Tetrahedron Lett. 1997, 38, 1275.
25. Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681.
26. (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1991, 32, 3095.
27. (b) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron: Asymmetry 1993, 4, 1603.
28. (c) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron 1994, 50, 4429.
29. (d) Inoue, I.; Shindo, M.; Koga, K.; Kanai, M.; Tomioka, K. Tetrahedron: Asymmetry 1995, 6, 2527.
30. (e) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Chem. Pharm. Bull. 1997, 45, 1705.
31. (f) Taniyama, D.; Kanai, M.; Iida, A.; Tomioka, K. Heterocycles 1997, 46, 165.
32. (g) Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron Lett. 2000, 41, 5533.
33. (h) Hasegawa, M.; Taniyama, D.; Tomioka, K. Tetrahedron 2000, 56, 10153.
34. (a) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
35. (b) Denmark, S. E.; Nakajima, N.; Nicaise, O. J. C.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884.
36. (c) Denmark, S. E.; Sttif, C. M. J. Org. Chem. 2000, 65, 5875.
37. (a) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097.
38. (b) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317.
39. (c) Hayase, T.; Inoue, Y.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2509.
40. (d) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519.
41. (e) Sato, I.; Kodaka, R.; Soai, K. J. Chem. Soc., Perkin Trans 1 2001, 2912.
42. (f) Sato, I.; Hosoi, K.; Kodaka, R.; Soai, K. Eur. J. Org. Chem. 2002, 3115.
43. (g) Soai, K.; Sato, I. C. R. Geoscience 2003, 6, 1097.
44. (a) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242.
45. (b) Bao, M.; Nakamura, H.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 131.
46. (c) Fernandes, R. A.; Stimac, A.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 14133.
47. (a) Nakamura, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 2614.
48. (b) Fernendes, R. A.; Yamamoto, Y. J. Org. Chem. 2004, 69, 735.
49. (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976.
50. (b) Hayashi, T.; Ishigetani, M. Tetrahedron 2001, 57, 2589.
51. (a) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
52. (b) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
53. (c) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
54. (d) Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63, 2541.
55. (e) Bäse, S.; Baumann, T.; Dahmen, S.; Vogt, H. Chem. Commun. 2007, 1881.
56. (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
57. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
58. (c) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382.
59. (d) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
60. (a) Fujihara, H.; Nagai, K.; Tomioka, K. J. Am. Chem. Soc. 2000, 122, 12055.
61. (b) Nagai, K.; Fujihara, H.; Kuriyama, M.; Yamada, K.; Tomioka, K. Chem. Lett. 2002, 8.
62. (c) Soeta, T.; Nagai, K.; Fujihara, H.; Kuriyama, M.; Tomioka, K. J. Org. Chem. 2003, 68, 9723.
63. Brown, B. R. In The Organic Chemistry of Aliphatic Nitrogen Compounds; Oxford University Press: Oxford. 1994.
64. Buncel, E.; Menon, B. J. Organomet. Chem. 1977, 141, 1.
65. Harned, H. S.; Robinson, R. A. Trans. Faraday Soc. 1944, 36, 973.
66. Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds; Pergamon Press: New York, 1982; p 823.
67. Reviews: (a) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
68. (b) Knochel, P. Synlett 1995, 393.
69. (c) Nakamura, M.; Nakamura, E. J. Synth. Org. Chem., Jpn. 1998, 56, 632.
70. (d) Knochel, P.; Perea, J. J. A.; Jones, P. Tetrahedron 1998, 54, 8275.
71. (e) Boudier, A.; Bromm, L. O.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414.
72. (a) Rozema, M. J.; Sidduri, A. R.; Knochel, P. J. Org. Chem. 1992, 57, 1956.
73. (b) Micouin, L.; Knochel, P. Synlett 1997, 327.
74. (c) Kneisel, F. F.; Dochnahl, M.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 1017.
75. (a) Rozema, M.; Eisenberg, C.; Lütjens, H.; Ostwald, R.; Belyk, K.; Knochel, P. Tetrahedron Lett. 1993, 34, 3115.
76. (b) Vettel, S.; Knochel, P. Tetrahedron Lett. 1994, 35, 5849.
77. Charette, A. B.; Beauchemin, A.; Marcoux, J.-F. J. Am. Chem. Soc. 1998, 120, 5114.
78. (a) Langer, F.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. Synlett 1994, 410.
79. (b) Langer, F.; Schwink, L.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. J. Org. Chem. 1996, 61, 8229.
80. (c) Boudier, A.; Darcel, C.; Flachsmann, F.; Micouin, L.; Oestreich, M.; Knochel, P. Chem. Eur. J. 2000, 6, 2748.
81. (d) Boudier, A.; Hupe, E.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2294.
82. (e) Hupe, E.; Knochel, P. Org. Lett. 2001, 3, 127.
83. (a) Vettel, S.; Vaupel, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 1023.
84. (b) Vettel, S.; Vaupel, A.; Knochel, P. J. Org. Chem. 1996, 61, 7473.
85. Reviews for copper-catalyzed asymmetric conjugate addition reactions: (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
86. (b) Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283.
87. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
88. (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221.
89. (e) López, F.; Minnaard, A. J.; Feringa, B. L. Acc. Chem. Res. 2006, 40, 179.
90. Reviews for enantioselective conjugate addition reactions: (a) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. III, Chapter 31.
91. (b) Tomioka, K. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 12.
92. (c) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
93. (d) Tomioka, K. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 2004; Supplement to Chapter 31.1, p 109.
94. (e) Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279.
95. Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427.
96. Fujihara, H. Ph.D. Thesis, Kyoto University, Japan, 2001.
97. (a) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692.
98. (b) Boezio, A. A.; Pytkowitz, J.; Côté, A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 14260. A review:
99. (c) Charette, A. B.; Boezio, A. A.; Côte, A.; Moreau, E.; Pytkowicz, J.; Desrosiers, J.-N.; Legault, C. Pure Appl. Chem. 2005, 77, 1259.
100. (a) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. J. Chem. Soc., Perkin Trans. 1 1985, 1217.
101. (b) Ramage, R.; Hopton, D.; Parrott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1984, 1357.
102. (a) Côté, A.; Coezio, A. A.; Charette, A. B. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5405.
103. (b) Desrosiers, J.-N.; Côté, A.; Charette, A. B. Tetrahedron 2005, 61, 6186.
104. Côté, A.; Charette, A. B. J. Org. Chem. 2005, 70, 10864.
105. Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873.
106. Lauzon, C.; Charette, A. B. Org. Lett. 2006, 8, 2743.
107. Pizzuti, M. G.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2008, 73, 940.
108. Arnold, L. A.; Imbos, R.; Mandoli, A.; de Varis, A. H. M.; Naasz, R.; Feringa, B. L. Tetrahedron 2000, 56, 2865.
109. Bisphosphine 51 can serve as a precursor of monoxide 31 when 51 is premixed with a copper salt before the addition of dialkylzinc reagent: Côte, A.; Boezio, A. A.; Charette, A. B. Angew. Chem., Int. Ed. 2004, 43, 6525.
110. Li, X.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Tetrahedron: Asymmetry 2003, 14, 3819.
111. Shi, M.; Zhang, W. Tetrahedron: Asymmetry 2003, 14, 3407.
112. A review: Zhang, W.; Shi, M. Synlett 2007, 19.
113. Wang, C.-J.; Shi, M. J. Org. Chem. 2003, 68, 6229.
114. (a) Shi, M.; Wang, C.-J. Adv. Synth. Catal. 2003, 345, 971.
115. (b) Shi, M.; Lei, Z.-Y.; Xu, Q. Adv. Synth. Catal. 2006, 348, 2237.
116. Wang, M.-C.; Xu, C.-L.; Zou, Y.-X.; Liu, H.-M.; Wang, D.-K. Tetrahedron Lett. 2005, 46, 5413.
117. A review: Arrayás, R. G.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 7674.
118. Wang, M.-C.; Liu, L.-T.; Hua, Y.-Z.; Zhang, J.-S.; Shi, Y.-Y.; Wang, D.-K. Tetrahedron: Asymmetry 2005, 16, 2531.
119. Wang, M.-C.; Xu, C.-L.; Cheng, F.; Ding, X. Tetrahedron 2006, 62, 12220.
120. (a) Kogen, H.; Tomioka, K.; Hashimoto, S.; Koga, K. Tetrahedron 1981, 37, 3951.
121. (b) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266.
122. (c) Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732.
123. (d) Shindo, M.; Koga, K.; Tomioka, K. J. Org. Chem. 1998, 63, 9351.
124. (e) Tomioka, K.; Shioya, Y.; Nagaoka, Y.; Yamada, K. J. Org. Chem. 2001, 66, 7051.
125. Soeta, T.; Kuriyama, M.; Tomioka, K. J. Org. Chem. 2005, 70, 297.
126. Palacios, F.; Vicario, J. Org. Lett. 2006, 8, 5405.
127. Esquivias, J.; Arrayás, R. G.; Carretero, J. C. J. Org. Chem. 2005, 70, 7451.
128. Ding, H.; Friestad, G. K. Synthesis 2005, 2815.
129. Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1995, 37, 8997.
130. (a) Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168.
131. (b) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67.
132. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844.
133. Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006.
134. Yao, S.; Fang, X.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1998, 2547.
135. Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687.
136. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
137. A review for the asymmetric arylation reactions: Bolm, C.; Hildebrand, J. P.; Muñz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284.
138. Hayashi, T.; Kawai, M.; Tokunaga, N. Angew. Chem., Int. Ed. 2004, 43, 6125.
139. (a) Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128.
140. (b) Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584.
141. (c) Weix, D. J.; Shi, Y.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092.
142. (d) Jagt, R. B. C.; Toullec, P. Y.; Geerdink, D.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Angew. Chem., Int. Ed. 2006, 45, 2789.
143. (e) Duan, H.; Jia, Y.; Wang, L.; Zhou, Q. Org. Lett. 2006, 8, 2567.
144. Reviews: (a) Jørgensen, K. A. Synthesis 2003, 1117.
145. (b) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550.
146. Johannsen, M. Chem. Commun. 1999, 2233.
147. (a) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114.
148. (b) Saaby, Bayón, P.; Aburel, P. S.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4352.
149. Jia, Y.-X.; Xie, J.-H.; Duan, H.-F.; Wang, L.-X; Zhou, Q.-L. Org. Lett. 2006, 8, 1621.
150. Luo, Y. M.; Li, C. J. Chem. Commun. 2004, 1930.
151. Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 45, 629.
152. Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
153. Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
154. Shirakawa, S.; Berger, R.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 2858.
155. A review for asymmetric addition of an alkynyl group to C=N double bonds: Zani, L.; Bohn, C. Chem. Commun. 2006, 4263.
156. Reviews: (a) Pu, L. Tetrahedron 2003, 59, 9873.
157. (b) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2004, 4095.
158. Frantz, D. E.; Fassler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245.
159. Jiang, B.; Si, Y.-G. Angew. Chem., Int. Ed. 2004, 43, 216.
160. Wei, W.; Kobayashi, M.; Ukaji, Y.; Inomata, K. Chem. Lett. 2006, 35, 176.
161. Zani, L.; Eichhorn, T.; Bolm, C. Chem. Eur. J. 2007, 13, 2587.
162. Sakaguchi, S.; Kubo, T.; Ishii, Y. Angew. Chem., Int. Ed. 2001, 40, 2534.
163. (a) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319.
164. (b) Fischer, C.; Carreira, E. M. Synthesis 2004, 1497.
165. Yamazaki, Y.; Fujita, K.; Yamaguchi, R. Chem. Lett. 2004, 33, 1316.
166. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
167. Kantam, M. L.; Prakash, B. V.; Reddy, C. R. V.; Sreedhar, B. Synlett 2005, 2329.
168. Lo, V. K.-Y.; Liu, Y.; Wong, M.-K.; Che, C.-M. Org. Lett. 2006, 8, 1529.
169. Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473.
170. Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42.
171. (a) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638.
172. (b) Wei, C.; Mague, J. T.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5749.
173. (c) Rosa, J. N.; Santos, A. G.; Afonso, C. A. M. J. Mol. Catal. A 2004, 214, 161.
174. (d) McDonagh, C.; O'Conghile, P.; Gebbink, R. J. M. K.; O'Leary, P. Tetrahedron Lett. 2007, 48, 4387.
175. Bisai, A.; Singh, V. Org. Lett. 2006, 8, 2405.
176. Ji, J.-X.; Wu, J.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11196.
177. Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
178. (a) Benaglia, M.; Negri, D.; Dell'Anna, G. Tetrahedron Lett. 2004, 45, 8705.
179. (b) Orlandi, S.; Colombo, F.; Benaglia, M. Synthesis 2005, 1689.
180. (c) Colombo, F.; Benaglia, M.; Orlandi, S.; Usuelli, F.; Celentano, G. J. Org. Chem. 2006, 71, 2064.
181. Hatano, M.; Asai, T.; Ishihara, K. Tetrahedron Lett. 2008, 49, 379.
182. Early report on CuCl-catalyzed alkynylation of enamine: Brannock, K. C.; Burpitt, R. D.; Thweatt, J. G. J. Org. Chem. 1963, 28, 1462.
183. (a) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
184. (b) Koradin, C.; Gommermann, N.; Polborn, K.; Knochel, P. Chem. Eur. J. 2003, 9, 2797.
185. (a) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763.
186. (b) Gommermann, N.; Knochel, P. Chem. Commun. 2004, 2324.
187. (c) Dube, H.; Gommermann, N.; Knochel, P. Synthesis 2004, 2015.
188. (d) Gommermann, N.; Gherig, A.; Knochel, P. Synlett 2005, 2796.
189. (6) Gommermann, N.; Knochel, P. Synlett 2005, 2799.
190. (f) Gommermann, N.; Knochel, P. Tetrahedron 2005, 61, 11418.
191. (g) Gommermann, N.; Knochel, P. Chem. Eur. J. 2006, 12, 4380.
192. Thomas, F.; Knöpfel, T. F.; Ichikawa, T.; Watanabe, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2004, 43, 5971.
193. Liu, B.; Liu, J.; Jia, X.; Huang, L.; Li, X.; Chan, A. S. C. Tetrahedron: Asymmetry 2007, 18, 1124.
194. Wu, T. R.; Chong, J. M. Org. Lett. 2006, 8, 15.
195. Gonzalez, A. Z.; Canales, E.; Soderquist, J. A. Org. Lett. 2006, 8, 3331.
196. Turcaud, S.; Berhal, F.; Royer, J. J. Org. Chem. 2007, 72, 7893.
197. (a) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984.
198. (b) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409.
199. (c) Akullian, L. C.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4244.
200. Akullian, L.; Porter, J.; Traverse, J.; Snapper, M.; Hoveyda, A. Adv. Synth. Catal. 2005, 347, 417.
201. Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2003, 5, 3237.
202. Basra, S.; Fennie, M.; Kozlowski, M. Org. Lett. 2006, 8, 2659.
203. A review on additives in asymmetric catalysis: Vogl, E. M.; Groger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570.
204. Nishimura, T.; Yasuhara, Y.; Hayashi, T. Org. Lett. 2006, 8, 979.
205. (a) Yamada, K.; Yamamoto, Y.; Maekawa, M.; Akindele, T.; Umeki, H.; Tomioka, K. Org. Lett. 2006, 8, 87.
206. (b) Almansa, R.; Guijarro, D.; Yus, M. Tetrahedron 2007, 63, 1167.
207. El-Shehawy, A. A. Tetrahedron: Asymmetry 2006, 17, 2617.
208. (a) Zhang, X.; Gong, L.; Mi, A.; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Let. 2001, 42, 6369.
209. (b) Zhang, H.-L.; Zhang, X.-M.; Gong, L.-Z.; Mi, A.-Q.; Cui, X.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2002, 4, 1399.
210. (c) Zhang, H.-L.; Jiang, F.; Zhang, X.-M.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Chem. Eur. J. 2004, 10, 1481.
211. Jimeno, C.; Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. Org. Lett. 2000, 2, 3157.
212. (a) Beresford, K. J. M. Tetrahedron Lett. 2002, 43, 7175.
213. (b) Beresford, K. J. M. Tetrahedron Lett. 2004, 45, 6041.
214. (a) Zhang, X.; Lin, W.; Gong, L.; Mi, A.; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 1535.
215. (b) Zhang, X.-M.; Zhang, H.-L.; Lin, W.-Q.; Gong, L.-Z.; Mi, A.-Q.; Cui, X.; Jiang, Y.-Z.; Yu, K.-B. J. Org. Chem. 2003, 68, 4322.
216. Almansa, R.; Guijarro, D.; Yus, M. Tetrahedron: Asymmetry 2007, 18, 896.
217. Dahmen, S.; Bräse, S. J. Am. Chem. Soc. 2002, 124, 5940.
218. Hermanns, N.; Dahmen, S.; Bohn, C.; Bräse, S. Angew. Chem., Int. Ed. 2002, 41, 3692.
219. (a) Zhang, H.-L.; Liu, H.; Cui, X.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. Synlett 2005, 615.
220. (b) Liu, H.; Zhang, H.-L.; Wang, S.-J.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. Tetrahedron: Asymmetry 2005, 16, 2901.
221. Reviews: (a) Yamada, K.; Yamamoto, Y.; Tomioka, K. J. Synth. Org. Chem., Jpn. 2004, 62, 1158.
222. (b) Bazin, S.; Feray, L.; Bertrand, M. P. Chima 2006, 60, 260.
223. Miyano, S.; Hashimoto, H. J. Chem. Soc. D: Chem. Commun. 1971, 1418.
224. Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335.
225. (a) Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. Synlett 1999, 1148.
226. (b) Bertrand, M. P.; Feray, R.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189.
227. (c) Bertrand, M. P.; Coantic, S.; Feray, L.; Nouguier, R.; Perfetti, P. Tetrahedron 2000, 56, 3951.
228. (d) Bazin, S.; Feray, L.; Siri, D.; Naubron, J.-V.; Bertrand, M. P. Chem. Commun. 2002, 2506.
229. (e) Bazin, S.; Feray, L.; Vanthuyne, N.; Bertrand, M. P. Tetrahedron 2005, 61, 4261.
230. (f) Bazin, S.; Feray, L.; Vanthuyne, N.; Siri, D.; Bertrand, M. P. Tetrahedron 2007, 63, 77.
231. (a) Miyabe, H.; Ushiro, C.; Ueda, M.; Yamakawa, K.; Naito, T. J. Org. Chem. 2000, 65, 176.
232. (b) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443.
233. (c) Miyabe, H.; Asada, R.; Yoshida, K.; Takemoto, Y. Synlett 2004, 540.
234. (d) Miyabe, H.; Asada, R.; Takemoto, Y. Tetrahedron 2005, 61, 385.
235. Feringa, B. L.; Kellog, R. M.; van der Deen, H. Org. Lett. 2000, 2, 1593.
236. (a) Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509.
237. (b) Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797.
238. (c) Yamamoto, Y.; Yamada, K.; Tomioka, K. Tetrahedron Lett. 2004, 45, 795.
239. (d) Yamada, K.; Yamamoto, Y.; Maekawa, M.; Tomioka, K. J. Org. Chem. 2004, 64, 1531.
240. (e) Yamada, K.; Yamamoto, Y.; Maekawa, M.; Chen, J.-B.; Tomioka, K. Tetrahedron Lett. 2004, 45, 6595.
241. (f) Yamamoto, Y.; Maekawa, M.; Akindele, T.; Yamada, K.; Tomioka, K. Tetrahedron 2005, 61, 379.
242. (g) Akindele, T.; Yamamoto, Y.; Maekawa, M.; Umeki, H.; Yamada, K.; Tomioka, K. Org. Lett. 2006, 8, 5729.
243. (a) Denes, F.; Chemla, F.; Normant, J. F. Angew. Chem., Int. Ed. 2003, 42, 4043.
244. (b) Denes, F.; Cutri, S.; Perez-Luna, A.; Chemla, F. Chem. Eur. J. 2006, 12, 6506.
245. Li, K.; Alexakis, A. Angew. Chem., Int. Ed. 2006, 45, 7600.