Stereoselective Synthesis of α-Branched Amines by Nucleophilic Addition of Unstabilized Carbanions to Imines

Chiral Amine Synthesis: Methods, Developments and Applications

Volumn , Issue , 2010, Pages 1-49

  Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

branched amines; Arylation; Carbanions; Chiral auxiliary; Imines; Nucleophilic addition

Indexed keywords

EID: 84886319348     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527629541.ch1     Document Type: Chapter

References (242)

1. Yamada, K. and Tomioka, K. (2008) Chem. Rev., 108, 2874
2. Friestad, G.K. and Mathies, A.K. (2007) Tetrahedron, 63, 2541
3. Ferraris, D. (2007) Tetrahedron, 63, 9581
4. Vilaivan, T., Bhanthumnavin, W., and Sritana-Anant, Y. (2005) Curr. Org. Chem., 9, 1315
5. Kobayashi, S. and Ishitani, H. (1999) Chem. Rev., 99, 1069
6. Bloch, R. (1998) Chem. Rev., 98, 1407
7. Enders, D. and Reinhold, U. (1997) Tetrahedron: Asymmetry, 8, 1895.
8. Deutsch, C., Krause, N., and Lipshutz, B.H., (2008) Chem. Rev., 108, 2916
9. Gladiali, S. and Alberico, E. (2006) Chem. Soc. Rev., 35, 226
10. Blaser, H.U., Malan, C., Pugin, B., Spindler, F., Steiner, H., and Studer, M. (2003) Adv. Synth. Catal., 345, 103.
11. Ukaji, Y., Watai, T., Sumi, T., and Fujisawa, T. (1991) Chem. Lett., 1555.
12. Takahashi, H., Chida, Y., Yoshii, T., Suzuki, T., and Yanaura, S. (1986) Chem. Pharm. Bull., 34, 2071.
13. Merino, P., Marqués-López, E., Tejero, T., and Herrera, R.P. (2009) Tetrahedron, 65, 1219
14. Gröger, H. (2003) Chem. Rev., 103, 2795.
15. Marques, M.M.B. (2006) Angew. Chem., Int. Ed., 45, 348
16. Mukherjee, S., Yang, J.W., Hoffmann, S., and List, B. (2007) Chem. Rev., 107, 5471
17. Verkade, J.M.M., van Hemert, L.J.C., Quaedflieg, P.J.L.M., and Rutjes, F.P.J.T. (2008) Chem. Soc. Rev., 37, 29.
18. Wessjohann, L.A., Rivera, D.G., and Vercillo, O.E. (2009) Chem. Rev., 109, 796
19. Domling, A. (2006) Chem. Rev., 106, 17
20. An, H.Y. and Cook, P.D. (2000) Chem. Rev., 100, 3311.
21. Charette, A.B., Boezio, A.A., Côté, A., Moreau, E., Pytkowicz, J., Desrosiers, J.-N., and Legault, C. (2005) Pure Appl. Chem., 77, 1259.
22. Colebourne, N., Foster, R.G., and Robson, E. (1967) J. Chem. Soc. C, 685
23. Mangeney, P., Tejero, T., Alexakis, A., Grosjean, F., and Normant, J. (1988) Synthesis, 255
24. Bigelow, L.A. and Eatough, H. (1941) Org. Synth., 1, 80
25. Taguchi, K. and Westheimer, F.H. (1971) J. Org. Chem., 36, 1570.
26. Enders, D. and Eichenauer, H. (1979) Chem. Ber., 112, 2933.
27. Zhizhin, A.A., Zarubin, D.N., and Ustynyuk, N.A. (2008) Tetrahedron Lett., 49, 699.
28. Davis, F.A., Reddy, R.T., and Reddy, R.E. (1992) J. Org. Chem., 57, 6387.
29. Annunziata, R., Cinquini, M., and Cozzi, F. (1982) J. Chem. Soc., Perkin Trans. 1, 339.
30. Liu, G.C., Cogan, D.A., Owens, T.D., Tang, T.P., and Ellman, J.A. (1999) J. Org. Chem., 64, 1278.
31. Trost, B.M. and Marrs, C. (1991) J. Org. Chem., 56, 6468.
32. Jennings, W.B. and Lovely, C.J. (1991) Tetrahedron, 47, 5561.
33. Wynne, J.H., Price, S.E., Rorer, J.R., and Stalick, W.M. (2003) Synth. Commun., 33, 341
34. Love, B.E., Raje, P.S., and Williams, T.C. II (1994) Synlett, 493.
35. Georg, G.I., Harriman, G.C.B., and Peterson, S.A. (1995) J. Org. Chem., 60, 7366.
36. Chemla, F., Hebbe, V., and Normant, J.-F. (2000) Synthesis, 75.
37. Artman, G.D., Bartolozzi, A., Franck, R.W., and Weinreb, S.M. (2001) Synlett, 232
38. Boger, D.L. and Corbett, W.L. (1992) J. Org. Chem., 57, 4777.
39. Ruano, J.L.G., Alemán, J., Cid, M.B., and Parra, A. (2005) Org. Lett., 7, 179.
40. Brown, C., Hudson, R.F., Maron, A., and Record, K.A. (1976) Chem. Commun., 663
41. Krzyzanowska, B. and Stec, W.J. (1978) Synthesis, 521.
42. Côté, A., Boezio, A.A., and Charette, A.B. (2004) Proc. Natl. Acad. Sci. USA, 101, 5405.
43. Yamaguchi, A., Matsunaga, S., and Shibasaki, M. (2006) Tetrahedron Lett., 47, 3985.
44. Kim, Y.H. and Shin, J.M. (1985) Tetrahedron Lett., 26, 3821.
45. Lauzon, C., Desrosiers, J.-N., and Charette, A.B. (2005) J. Org. Chem., 70, 10579.
46. Lauzon, C. and Charette, A.B. (2006) Org. Lett., 8, 2743.
47. Hart, D.J., Kanai, K., Thomas, D.G., and Yang, T.K. (1983) J. Org. Chem., 48, 289
48. Vidal, J., Damestoy, S., Guy, L., Hannachi, J.C., Aubry, A., and Collet, A. (1997) Chem. Eur. J., 3, 1691
49. Kupfer, R., Meier, S., and Würthwein, E.-U. (1984) Synthesis, 688.
50. Petrini, M. (2005) Chem. Rev., 105, 3949.
51. Ballini, R. and Petrini, M. (1999) Tetrahedron Lett., 40, 4449
52. Olijnsma, T., Engberts, J.B.F.N., and Strating, J. (1967) Recl. Trav. Chim. Pays-Bas, 86, 463.
53. Kanazawa, A.M., Denis, J.N., and Greene, A.E. (1994) J. Org. Chem., 59, 1238.
54. Enders, D. and Reinhold, U. (1997) Tetrahedron: Asymmetry, 8, 1895
55. Davis, F.A., Zhou, P., and Chen, B.C. (1998) Chem. Soc. Rev., 27, 13
56. Alvaro, G. and Savoia, D. (2002) Synlett, 651
57. Ellman, J.A., Owens T.D., and Tang, T.P. (2002) Acc. Chem. Res., 35, 984
58. Zhou, P., Chen, B.C., and Davis, F.A. (2004) Tetrahedron, 60, 8003
59. Friestad, G.K. (2005) Eur. J. Org. Chem., 3157.
60. Alexakis, A., Lensen, N., and Mangeney, P. (1991) Tetrahedron Lett., 32, 1171
61. Alexakis, A., Tranchier, J.P., Lensen, N., and Mangeney, P. (1995) J. Am. Chem. Soc., 117, 10767
62. Thiam, M. and Chastrette, F. (1992) Bull. Chem. Soc. Fr., 129, 161
63. Matsubara, S., Ukita, H., Kodama, T., and Utimoto, K. (1994) Chem. Lett., 831
64. Badorrey, R., Cativiela, C., Diaz-de-Villegas, M.D., and Galvez, J.A. (1997) Tetrahedron, 53, 1411.
65. Charette, A.B. and Mellon, C. (1998) Tetrahedron, 54, 10525.
66. Vogt, H. and Bräse, S. (2007) Org. Biomol. Chem., 5, 406
67. Cativiela, C. and Díaz-de-Villegas, M.D. (2007) Tetrahedron: Asymmetry, 18, 569.
68. Alvaro, G., Savoia, D., and Valentinetti, M.R. (1996) Tetrahedron, 52, 12571.
69. Beuchet, P., Lemarrec, N., and Mosset, P. (1992) Tetrahedron Lett., 33, 5959
70. Wang, D.K., Dai, L.X., and Hou, X.L. (1995) Tetrahedron Lett., 36, 8649
71. Wang, D.K., Dai, L.X., Hou, X.L., and Zhang, Y. (1996) Tetrahedron Lett., 37, 4187
72. Gao, Y.A. and Sato, F. (1995) J. Org. Chem., 60, 8136.
73. Wakchaure, V.N., Mohanty, R.r., Shaikh, A.J., and Nugent, T.C. (2007) Eur. J. Org. Chem., 959.
74. Takahashi, H., Chida, Y., Higashiyama, K., and Onishi, H. (1985) Chem. Pharm. Bull., 33, 4662
75. Takahashi, H., Chida, Y., Suzuki, T., Onishi, H., and Yanaura, S. (1984) Chem. Pharm. Bull., 32, 2714
76. Takahashi, H., Suzuki, Y., and Hori, T. (1983) Chem. Pharm. Bull., 31, 2183
77. Takahashi, H., Chida, Y., Suzuki, T., Yanaura, S., Suzuki, Y., and Masuda, C. (1983) Chem. Pharm. Bull., 31, 1659
78. Suzuki, Y. and Takahashi, H. (1983) Chem. Pharm. Bull., 31, 2895
79. Suzuki, Y. and Takahashi, H. (1983) Chem. Pharm. Bull., 31, 31
80. Takahashi, H., Suzuki, Y., and Inagaki, H. (1982) Chem. Pharm. Bull., 30, 3160.
81. Muralidharan, K.R., Mokhallalati, M.K., and Pridgen, L.N. (1994) Tetrahedron Lett., 35, 7489
82. Mokhallalati, M.K. and Pridgen, L.N. (1993) Synth. Commun., 23, 2055
83. Pridgen, L.N., Mokhallalati, M.K., and Wu, M.J. (1992) J. Org. Chem., 57, 1237
84. Wu, M.J. and Pridgen, L.N. (1991) J. Org. Chem., 56, 1340
85. Wu, M.J. and Pridgen, L.N. (1990) Synlett, 636.
86. Tanaka, H., Inoue, K., Pokorski, U., Taniguchi, M., and Torii, S. (1990) Tetrahedron Lett., 31, 3023.
87. Laschat, S. and Kunz, H. (1990) Synlett, 51.
88. Takahashi, H., Tomita, K., and Otomasu, H. (1979) J. Chem. Soc., Chem. Commun., 668
89. Takahashi, H., Tomita, K., and Noguchi, H. (1981) Chem. Pharm. Bull., 29, 3387
90. Takahashi, H. and Inagaki, H. (1982) Chem. Pharm. Bull., 30, 922
91. Takahashi, H. and Suzuki, Y. (1983) Chem. Pharm. Bull., 31, 4295.
92. For a review of the chemistry of SAMP and RAMP, see Job, A., Janeck, C.F., Bettray, W., Peters, R., and Enders, D. (2002) Tetrahedron, 58, 2253.
93. Enders, D., Schubert, H., and Nubling, C. (1986) Angew. Chem., Int. Ed., 25, 1109.
94. Denmark, S.E., Weber, T., and Piotrowski, D.W. (1987) J. Am. Chem. Soc., 109, 2224
95. Denmark, S.E., Edwards, J.P., and Nicaise, O. (1993) J. Org. Chem., 58, 569.
96. Friestad, G.K. and Ding, H. (2001) Angew. Chem., Int. Ed., 40, 4491.
97. For a review on acyl hydrazone chemistry, see Sugiura, M. and Kobayashi, S. (2005) Angew. Chem., Int. Ed., 44, 5176.
98. Brown, D.S., Gallagher, P.T., Lightfoot, A.P., Moody, C.J., Slawin, A.M.Z., and Swann, E. (1995) Tetrahedron, 51, 11473
99. Gallagher, P.T., Lightfoot, A.P., Moody, C.J., and Slawin, A.M.Z. (1995) Synlett, 445.
100. Moreau, P., Essiz, M., Merour, J.Y., and Bouzard, D. (1997) Tetrahedron: Asymmetry, 8, 591.
101. Koriyama, Y., Nozawa, A., Hayakawa, R., and Shimizu, M. (2002) Tetrahedron, 58, 9621.
102. Wipf, P., Nunes, R.L., and Ribe, S. (2002) Helv. Chim. Acta, 85, 3478.
103. Li, G.G., Wei, H.X., Whittlesey, B.R., and Batrice, N.N. (1999) J. Org. Chem., 64, 1061.
104. For other examples of allylation and crotylation using trifluoroborate reagents, see Li, S.W. and Batey, R.A. (2004) Chem. Commun., 1382.
105. Weix, D.J. and Ellman, J.A. (2003) Org. Lett., 5, 1317.
106. Liu, G.C., Cogan, D.A., and Ellman, J.A. (1997) J. Am. Chem. Soc., 119, 9913
107. Cogan, D.A., Liu, G.C., and Ellman, J. (1999) Tetrahedron, 55, 8883.
108. For the preparation of a library of α-branched amines, see Mukade, T., Dragoli, D.R., and Ellman, J.A. (2003) J. Comb. Chem., 5, 590.
109. For the preparation of aza-Morita-Baylis-Hillman, see Reynolds, T.E., Binkley, M.S., and Scheidt, K.A. (2008) Org. Lett., 10, 5227.
110. Ding, C.H., Chen, D.D., Luo, Z.B., Dai, L.X., and Hou, X.L. (2006) Synlett, 1272.
111. For diastereoselective addition reactions of trialkoxysilylalkynes to N-tertbutanesulfinyl imines, see Lettan, R.B. and Scheidt, K.A. (2005) Org. Lett., 7, 3227.
112. Weix, D.J., Shi, Y.L., and Ellman, J.A. (2005) J. Am. Chem. Soc., 127, 1092
113. Beenen, M.A., Weix, D.J., and Ellman, J.A. (2006) J. Am. Chem. Soc., 128, 6304
114. Bolshan, Y. and Batey, R.A. (2005) Org. Lett., 7, 1481.
115. Kong, J.R., Cho, C.W., and Krische, M.J. (2005) J. Am. Chem. Soc., 127, 11269.
116. Steinig, A.G. and Spero, D.M. (1999) J. Org. Chem., 64, 2406
117. Spero, D.M. and Kapadia, S.R. (1997) J. Org. Chem., 62, 5537.
118. Cogan, D.A. and Ellman, J.A. (1999) J. Am. Chem. Soc., 121, 268.
119. For an application of this methodology, see Shaw, A.W. and deSolms, S.J. (2001) Tetrahedron Lett., 42, 7173.
120. Patterson, A.W. and Ellman, J.A. (2006) J. Org. Chem., 71, 7110.
121. Tomioka, K., Inoue, I., Shindo, M., and Koga, K. (1991) Tetrahedron Lett., 32, 3095
122. Tomioka, K., Inoue, I., Shindo, M., and Koga, K. (1990) Tetrahedron Lett., 31, 6681.
123. Soai, K., Hatanaka, T., and Miyazawa, T. (1992) Chem. Commun., 1097.
124. Denmark, S.E., Nakajima, N., and Nicaise, O.J.C. (1994) J. Am. Chem. Soc., 116, 8797
125. Denmark, S.E. and Nicaise, O.J.C. (1996) Chem. Commun., 999
126. Denmark, S.E., Nakajima, N., Stiff, C.M., Nicaise, O.J.C., and Kranz, M. (2008) Adv. Synth. Catal., 350, 1023.
127. Denmark, S.E. and Stiff, C.M. (2000) J. Org. Chem., 65, 5875
128. Denmark, S.E., Nakajima, N., Nicaise, O.J.C., Faucher, A.M., and Edwards, J.P. (1995) J. Org. Chem., 60, 4884.
129. Fujihara, H., Nagai, K., and Tomioka, K. (2000) J. Am. Chem. Soc., 122, 12055
130. Nagai, K., Fujihara, H., Kuriyama, M., Yamada, K., and Tomioka, K. (2002) Chem. Lett., 8
131. Soeta, T., Nagai, K., Fujihara, H., Kuriyama, M., and Tomioka, K. (2003) J. Org. Chem., 68, 9723.
132. de Vries, A.H.M., Meetsma, A., and Feringa, B.L. (1996) Angew. Chem., Int. Ed., 35, 2374
133. Alexakis, A., Vastra, J., and Mangeney, P. (1997) Tetrahedron Lett., 38, 7745.
134. Wang, M.C., Xu, C.L., Zou, Y.X., Liu, H.M., and Wang, D.K. (2005) Tetrahedron Lett., 46, 5413
135. Li, X., Cun, L.F., Gong, L.Z., Mi, A.Q., and Jiang, Y.Z. (2003) Tetrahedron: Asymmetry, 14, 3819
136. Wang, C.J. and Shi, M. (2003) J. Org. Chem., 68, 6229
137. Shi, M. and Zhang, W. (2003) Tetrahedron: Asymmetry, 14, 3407.
138. Boezio, A.A. and Charette, A.B. (2003) J. Am. Chem. Soc., 125, 1692
139. Boezio, A.A., Pytkowicz, J., Côté, A., and Charette, A.B. (2003) J. Am. Chem. Soc., 125, 14260
140. Côté, A. and Charette, A.B. (2005) J. Org. Chem., 70, 10864
141. Desrosiers, J.-N., Côté, A., and Charette, A.B. (2005) Tetrahedron, 61, 6186
142. Charette, A.B., Côté, A., Desrosiers, J.-N., Bonnaventure, I., Lindsay, V.N.G., Lauzon, C., Tannous, J., and Boezio, A.A. (2008) Pure Appl. Chem., 80, 881
143. Bonnaventure, I. and Charette, A.B. (2008) J. Org. Chem., 73, 6330.
144. Shi, M. and Wang, C.J. (2003) Adv. Synth. Catal., 345, 971
145. Wang, M.C., Liu, L.T., Hua, Y.Z., Zhang, J.S., Shi, Y.Y., and Wang, D.K. (2005) Tetrahedron: Asymmetry, 16, 2531
146. Kim, B.S., Kang, S.W., Kim, K.H., Ko, D.H., Chung, Y., and Ha, D.C. (2005) Bull. Korean Chem. Soc., 26, 1501
147. Chen, J.M., Li, D., Ma, H.F., Cun, L.F., Zhu, J., Deng, J.G., and Liao, J. (2008) Tetrahedron Lett., 49, 6921.
148. Côté, A. and Charette, A.B. (2008) J. Am. Chem. Soc., 130, 2771.
149. Pizzuti, M.G., Minnaard, A.J., and Feringa, B.L. (2008) J. Org. Chem., 73, 940.
150. Andersson, P.G., Guijarro, D., and Tanner, D. (1997) J. Org. Chem., 62, 7364
151. Brandt, P., Hedberg, C., Lawonn, K., Pinho, P., and Andersson, P.G. (1999) Chem. Eur. J., 5, 1692.
152. Rozenberg, V., Danilova, T., Sergeeva, E., Vorontsov, E., Starikova, Z., Lysenko, K., and Belokon, Y. (2000) Eur. J. Org. Chem., 3295
153. Cipiciani, A., Fringuelli, F., Mancini, V., Piermatti, O., Scappini, A.M., and Ruzziconi, R. (1997) Tetrahedron, 53, 11853
154. Cipiciani, A., Fringuelli, F., Mancini, V., Piermatti, O., Pizzo, F., and Ruzziconi, R. (1997) J. Org. Chem., 62, 3744.
155. Dahmen, S. and Bräse, S. (2002) J. Am. Chem. Soc., 124, 5940.
156. Porter, J.R., Traverse, J.F., Hoveyda, A.H., and Snapper, M.L. (2001) J. Am. Chem. Soc., 123, 984.
157. Porter, J.R., Traverse, J.F., Hoveyda, A.H., and Snapper, M.L. (2001) J. Am. Chem. Soc., 123, 10409
158. Akullian, L.C., Snapper, M.L., and Hoveyda, A.H. (2003) Angew. Chem., Int. Ed., 42, 4244.
159. Akullian, L.C., Porter, J.R., Traverse, J.E., Snapper, M.L., and Hoveyda, A.H. (2005) Adv. Synth. Catal., 347, 417.
160. Fu, P., Snapper, M.L., and Hoveyda, A.H. (2008) J. Am. Chem. Soc., 130, 5530.
161. A titanium-catalyzed asymmetric addition of diorganozinc to aaldiminoesters was shown to proceed with moderate level of enantioselectivities: Basra, S., Fennie, M.W., and Kozlowski, M.C., (2006) Org. Lett., 8, 2659.
162. Nishimura, T., Yasuhara, Y., and Hayashi, T. (2006) Org. Lett., 8, 979.
163. Chataigner, I., Zammattio, F., Lebreton, J., and Villieras, J. (1998) Synlett, 275
164. Itsuno, S., Yokoi, A., and Kuroda, S. (1999) Synlett, 1987
165. Sugiura, M., Hirano, K., and Kobayashi, S. (2004) J. Am. Chem. Soc., 126, 7182
166. Wu, T.R. and Chong, J.M. (2006) J. Am. Chem. Soc., 128, 9646
167. Canales, E., Hernandez, E., and Soderquist, J.A. (2006) J. Am. Chem. Soc., 128, 8712
168. Chataigner, I., Zammattio, F., Lebreton, J., and Villiéras, J. (2008) Tetrahedron, 64, 2441.
169. Panek, J.S. and Jain, N.F. (1994) J. Org. Chem., 59, 2674
170. Schaus, J.V., Jain, N., and Panek, J.S. (2000) Tetrahedron, 56, 10263
171. Berger, R., Rabbat, P.M.A., and Leighton, J.L. (2003) J. Am. Chem. Soc., 125, 9596
172. Berger, R., Duff, K., and Leighton, J.L. (2004) J. Am. Chem. Soc., 126, 5686.
173. Hanessian, S. and Yang, R.Y. (1996) Tetrahedron Lett., 37, 8997
174. Nakamura, M., Hirai, A., and Nakamura, E. (1996) J. Am. Chem. Soc., 118, 8489.
175. Cook, G.R., Kargbo, R., and Maity, B. (2005) Org. Lett., 7, 2767.
176. Itsuno, S., Watanabe, K., Ito, K., El-Shehawy, A.A., and Sarhan, A.A. (1997) Angew. Chem., Int. Ed., 36, 109.
177. Chen, G.M., Ramachandran, P.V., and Brown, H.C. (1999) Angew. Chem., Int. Ed., 38, 825.
178. Ramachandran, P.V. and Burghardt, T.E. (2005) Chem. Eur. J., 11, 4387.
179. Nakamura, H., Nakamura, K., and Yamamoto, Y. (1998) J. Am. Chem. Soc., 120, 4242
180. Nakamura, K., Nakamura, H., and Yamamoto, Y. (1999) J. Org. Chem., 64, 2614
181. Fernandes, R.A., Stimac, A., and Yamamoto, Y. (2003) J. Am. Chem. Soc., 125, 14133;
182. Fernandes, R.A. and Yamamoto, Y. (2004) J. Org. Chem., 69, 3562
183. Fernandes, R.A. and Yamamoto, Y. (2004) J. Org. Chem., 69, 735.
184. Gastner, T., Ishitani, H., Akiyama, R., and Kobayashi, S. (2001) Angew. Chem., Int. Ed., 40, 1896.
185. Tan, K.L. and Jacobsen, E.N. (2007) Angew. Chem., Int. Ed., 46, 1315.
186. Lou, S., Moquist, P.N., and Schaus, S.E. (2007) J. Am. Chem. Soc., 129, 15398.
187. Wada, R., Shibuguchi, T., Makino, S., Oisaki, K., Kanai, M., and Shibasaki, M. (2006) J. Am. Chem. Soc., 128, 7687.
188. Fang, X.M., Johannsen, M., Yao, S.L., Gathergood, N., Hazell, R.G., and Jørgensen, K.A. (1999) J. Org. Chem., 64, 4844.
189. Ferraris, D., Dudding, T., Young, B., Drury, W.J., and Lectka, T. (1999) J. Org. Chem., 64, 2168.
190. Hamada, T., Manabe, K., and Kobayashi, S. (2003) Angew. Chem., Int. Ed., 42, 3927.
191. Schneider, U., Chen, I.H., and Kobayashi, S. (2008) Org. Lett., 10, 737.
192. Patel, S.J. and Jamison, T.F. (2004) Angew. Chem., Int. Ed., 43, 3941
193. Patel, S.J. and Jamison, T.F. (2003) Angew. Chem., Int. Ed., 42, 1364.
194. Ngai, M.Y., Barchuk, A., and Krische, M.J. (2007) J. Am. Chem. Soc., 129, 12644.
195. Skucas, E., Kong, J.R., and Krische, M.J. (2007) J. Am. Chem. Soc., 129, 7242.
196. Petasis, N.A. and Zavialov, I.A. (1997) J. Am. Chem. Soc., 119, 445
197. Harwood, L.M., Currie, G.S., Drew, M.G.B., and Luke, R.W.A. (1996) Chem. Commun., 1953
198. Koolmeister, T., Sodergren, M., and Scobie, M. (2002) Tetrahedron Lett., 43, 5969
199. Nanda, K.K. and Trotter, B.W. (2005) Tetrahedron Lett., 46, 2025
200. Southwood, T.J., Curry, M.C., and Hutton, C.A. (2006) Tetrahedron, 62, 236.
201. Lou, S. and Schaus, S.E. (2008) J. Am. Chem. Soc., 130, 6922.
202. Nehl, H. and Scheidt, W.R. (1985) J. Organomet. Chem., 289, 1
203. Oppolzer, W. and Radinov, R.N. (1992) Helv. Chim. Acta, 75, 170
204. Lutz, C. and Knochel, P. (1997) J. Org. Chem., 62, 7895.
205. Hermanns, N., Dahmen, S., Bolm, C., and Bräse, S. (2002) Angew. Chem., Int. Ed., 41, 3692.
206. Hayashi, T. and Ishigedani, M. (2001) Tetrahedron, 57, 2589
207. Hayashi, T. and Ishigedani, M. (2000) J. Am. Chem. Soc., 122, 976.
208. Hayashi, T., Kawai, M., and Tokunaga, N. (2004) Angew. Chem., Int. Ed., 43, 6125.
209. Ueda, M., Saito, A., and Miyaura, N. (2000) Synlett, 1637
210. Ueda, M. and Miyaura, N. (2000) J. Organomet. Chem., 595, 31.
211. Kuriyama, M., Soeta, T., Hao, X.Y., Chen, O., and Tomioka, K. (2004) J. Am. Chem. Soc., 126, 8128.
212. Duan, H.-F., Jia, Y.-X., Wang, L.-X., and Zhou, Q.-L. (2006) Org. Lett., 8, 2567.
213. Kurihara, K., Yamamoto, Y., and Miyaura, N. (2009) Adv. Synth. Catal., 351, 260.
214. Trincado, M. and Ellman, J.A. (2008) Angew. Chem., Int. Ed., 47, 5623.
215. Nakagawa, H., Rech, J.C., Sindelar, R.W., and Ellman, J.A. (2007) Org. Lett., 9, 5155.
216. Jagt, R.B.C., Toullec, P.Y., Geerdink, D., de Vries, J.G., Feringa, B.L., and Minnaard, A.D.J. (2006) Angew. Chem., Int. Ed., 45, 2789.
217. Tokunaga, N., Otomaru, Y., Okamoto, K., Ueyama, K., Shintani, R., and Hayashi, T. (2004) J. Am. Chem. Soc., 126, 13584.
218. Otomaru, Y., Tokunaga, N., Shintani, R., and Hayashi, T. (2005) Org. Lett., 7, 307.
219. Huffman, M.A., Yasuda, N., Decamp, A.E., and Grabowski, E.J.J. (1995) J. Org. Chem., 60, 1590
220. Kauffman, G.S., Harris, G.D., Dorow, R.L., Stone, B.R.P., Parsons, R.L., Pesti, J.A., Magnus, N.A., Fortunak, J.M., Confalone, P.N., and Nugent, W.A. (2000) Org. Lett., 2, 3119
221. Frantz, D.E., Fassler, R., and Carreira, E.M. (1999) J. Am. Chem. Soc., 121, 11245.
222. For example, see Wu, T.R. and Chong, J.M. (2006) Org. Lett., 8, 15.
223. Wei, C.M., Mague, J.T., and Li, C.J. (2004) Proc. Natl. Acad. Sci. USA, 101, 5749
224. Wei, C.M. and Li, C.J. (2002) J. Am. Chem. Soc., 124, 5638.
225. For a related silver-catalyzed reaction that proceeds in lower ee's, see Ji, J.X., Wu, J., and Chan, A.S.C. (2005) Proc. Natl. Acad. Sci. USA, 102, 11196.
226. Colombo, F., Benaglia, M., Orlandi, S., Usuelli, F., and Celentano, G. (2006) J. Org. Chem., 71, 2064
227. Orlandi, S., Colombo, F., and Benaglia, M. (2005) Synthesis, 1689
228. Benaglia, M., Negri, D., and Dell'Anna, G. (2004) Tetrahedron Lett., 45, 8705
229. Bisai, A. and Singh, V.K. (2006) Org. Lett., 8, 2405
230. Liu, B., Huang, L., Liu, J.T., Zhong, Y., Li, X.S., and Chan, A.S.C. (2007) Tetrahedron: Asymmetry, 18, 2901
231. Hatano, M., Asai, T., and Ishihara, K. (2008) Tetrahedron Lett., 49, 379
232. Irmak, M. and Boysen, M.M.K. (2008) Adv. Synth. Catal., 350, 403.
233. Koradin, C., Polborn, K., and Knochel, P. (2002) Angew. Chem., Int. Ed., 41, 2535
234. Koradin, C., Gommermann, N., Polborn, K., and Knochel, P. (2003) Chem. Eur. J., 9, 2797
235. Gommermann, N. and Knochel, P. (2004) Chem. Commun., 2324
236. Gommermann, N. and Knochel, P. (2005) Synlett, 2799
237. Gommermann, N. and Knochel, P. (2006) Chem. Eur. J., 12, 4380.
238. Gommermann, N., Koradin, X., Polborn, K., and Knochel, P. (2003) Angew. Chem., Int. Ed., 42, 5763.
239. Gommermann, N. and Knochel, P. (2005) Chem. Commun., 4175.
240. Knöpfel, T.F., Aschwanden, P., Ichikawa, T., Watanabe, T., and Carreira, E.M. (2004) Angew. Chem., Int. Ed., 43, 5971
241. Aschwanden, P., Stephenson, C.R.J., and Carreira, E.M. (2006) Org. Lett., 8, 2437.
242. Traverse, J.F., Hoveyda, A.H., and Snapper, M.L. (2003) Org. Lett., 5, 3273.