Iminium catalysis

Chemical Reviews

Volumn 107, Issue 12, 2007, Pages 5416-5470

  Erkkilä, Anniina ^a   Majander, Inkeri ^a   Pihko, Petri M ^a  

^a AALTO UNIVERSITY   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; CYCLOADDITION; IONS;

CATALYTIC CYCLE; IMINIUM; KNOEVENAGEL REACTIONS; MANNICH REACTIONS;

ORGANIC COMPOUNDS;

ALDEHYDE; ETHER DERIVATIVE; IMINE; ION; KETONE;

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

ALDEHYDES; CATALYSIS; CYCLIZATION; ETHERS; IMINES; IONS; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 38349178582     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr068388p     Document Type: Review

References (329)

1. List, B. Synlett 2001, 1675.
2. Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
3. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
4. Bolm, C.; Rantanen, T.; Schiffers, I.; Zani, L. Angew. Chem., Int. Ed. 2005, 44, 1758.
5. Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
6. Adolfsson, H. Angew. Chem., Int. Ed. 2005, 44, 3340.
7. Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354.
8. Lelais, G.; MacMillan, D. W. C. Aldrichim. Acta 2006, 39, 79.
9. List, B. Chem. Commun. 2006, 819.
10. Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876.
11. For excellent reviews on the subject of immobilized catalysts, see: (a) Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 103, 3401.
12. (b) Cozzi, F. Adv. Synth. Catal. 2006, 348, 1367.
13. Gaunt, M. J.; Johansson, C. C. C.; McNally, A.; Vo, N. T. Drug Discovery Today 2007, 12, 8.
14. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
15. Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
16. Almaşi, D.; Alonso, D. A.; Nájera, C. Tetrahedron: Asymmetry 2007, 18, 299.
17. For books on iminium catalysis, see: a) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005.
18. b) Dalko, P. I., Ed. Enantioselective Organocatalysis: Reactions and Experimental Procedures, Wiley-VCH, Weinheim, 2007.
19. c) MacMillan, D. W. C.; Lelais, G. In New Frontiers in Asymmetric Catalysis; Mikami, K.; Lautens, M., Eds.; John Wiley & Sons, Hoboken, NJ, 2007.
20. For a review of the Knoevenagel reaction, see: Tietze, L. F.; Beifuss, U. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 2, p 341.
21. Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1045, and references therein.
22. Layer, R. W. Chem. Rev. 1963, 63, 489.
23. Schiff, H. Liebigs Ann. 1864, 131, 118.
24. Brown, H. C., et al. In Determination of Organic Structures Physical Methods; Braude, E. A., Nachod, F. C., Eds.; Academic Press: New York, 1955.
25. Of course, most of the early contributions describe relatively patchy observations rather than generalized concepts. However, it should be remembered that the development of more general concepts always requires an intellectual framework as well as an experimental background to build on. As an example, in their seminal 1928 paper on the discovery of the Diels - Alder reaction (Diels, O.; Alder, K. Liebigs Ann. 1928, 460, 98), Diels and Alder could not have used modern concepts like HOMO or LUMO - these terms simply did not exist! The general orbital symmetry and frontier orbital descriptions came much later, and today the Diels - Alder reaction is properly classified as an all-suprafacial [4+2]-cycloaddition.
26. Knoevenagel, E. Chem. Ber. 1894, 27, 2345.
27. Knoevenagel, E. Chem. Ber. 1898, 31, 2596. Although Knoevenagel did not suggest discrete iminium intermediates, he nevertheless recognized that the condensation products between aldehydes and the amine catalysts might play a role in these reactions.
28. Blanchard, K. C.; Klein, D. L.; MacDonald, J. J. Am. Chem. Soc. 1931, 53, 2809.
29. Crowell, T. I.; Peck, D. W. J. Am. Chem. Soc. 1953, 75, 1075.
30. Pollak, E. Beitr. Chem. Physiol. Pathol. ("Hofmeisters Beiträge") 1907, 10, 232.
31. Widmark, E. M. P.; Jeppsson, C. A. Skand. Arch. Physiol. 1922, 42, 43.
32. Pedersen, K. J. J. Phys. Chem. 1934, 38, 559.
33. Pedersen, K. J. J. Am. Chem. Soc. 1938, 60, 595.
34. Westheimer, F. H.; Cohen, H. J. Am. Chem. Soc. 1938, 60, 90.
35. Hamilton, G. A.; Westheimer, F. H. J. Am. Chem. Soc. 1959, 81, 6332.
36. Langenbeck, W.; Sauerbier, R. Chem. Ber. 1937, 70, 1540.
37. Langenbeck even went on to write a textbook on organocatalysis in 1935. Its second edition, published in 1949, oddly enough does not include any mention of the work of Pollak, Widmark, or Pedersen. Nevertheless, the book is a landmark historical source for the early development of organocatalysis. Langenbeck credits Wilhelm Ostwald as the father of the term organocatalyst (organische Katalysator): Ostwald, W. Z. Phys. Chem. 1900, 34, 510.
38. See: Langenbeck, W. Die organishen Katalysatoren und ihre Beziehungen zu den Fermenten (Organic Catalysts and Their Relation to the Enzymes), 2nd ed.; Springer: Berlin, 1949.
39. Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B.-W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H.; Chênevert, R. B.; Fliri, A.; Frobel, K.; Gais, H.-J.; Garratt, D. G.; Hayakawa, K.; Heggie, W.; Hesson, D. P.; Hoppe, D.; Hoppe, I.; Hyatt, J. A.; Ikeda, D.; Jacobi, P. A.; Kim, K. S.; Kobuke, Y.; Kojima, K.; Krowicki, K.; Lee, V. J.; Lautert, T.; Malchenko, S.; Martens, J.; Matthews, R. S.; Ong, B. S.; Press, J. B.; Rajan Babu, T. V.; Rousseau, G.; Sauter, H. M.; Suzuki, M.; Tatsuta, K.; Tolbert, L. M.; Truesdale, E. A.; Uchida, I.; Ueda, Y.; Uyehara, T.; Vasella, A. T.; Vladuchick, W. C.; Wade, P. A.; Williams, R. M.; Wong, H. N.-C. J. Am. Chem. Soc. 1981, 103, 3210.
40. Yamaguchi, M.; Yokota, N.; Minami, T. J. Chem. Soc., Chem. Commun. 1991, 1088.
41. Cordes, E. H.; Jencks, W. P. J. Am. Chem. Soc. 1962, 84, 826.
42. Fridovich, I.; Westheimer, F. H. J. Am. Chem. Soc. 1962, 84, 3208.
43. For selected examples, see: (a) Hine, J.; Houston, J. G. Jensen, J. H.; Mulders, J. J. Am. Chem. Soc. 1965, 87, 5050.
44. (b) Hine, J.; Menon, B. C.; Jensen, J. H.; Mulders, J. J. Am. Chem. Soc. 1966, 88, 3367.
45. For examples, see: (a) Hupe, D. J.; Kendall, M. C. R.; Spencer, T. A. J. Am. Chem. Soc. 1972, 94, 1254.
46. (b) Ferran, H. E., Jr.; Roberts, R. D.; Jacob, J. N.; Spencer, T. A. J. Chem Soc., Chem. Commun. 1978, 49.
47. (c) For an important early account on iminium catalysis in enamine formation, see: Spencer, T. A. Bioorg. Chem. 1977, 1, 313.
48. For selected examples, see: (a) Yasnikov, A. A. Organicheskie Katalizatory, Kofermenty i Fermenty, Rub. 3; Naukova Dumka: Kiev, 1982.
49. (b) Mushketik, L. S.; Volkova, N. V.; Shilov, E. A.; Yasnikov, A. A. Ukr. Khim. Zh. 1972, 38, 1259.
50. (c) Mel'nichenko, I. V.; Kozlova, N. Y.; Yasnikov, A. A. Ukr. Khim. Zh. 1982, 48, 1211.
51. For example, see: Williams, A.; Bender, M. L. J. Am. Chem. Soc. 1966, 88, 2508.
52. Baum, J. S.; Viehe, H. G. J. Org. Chem. 1976, 41, 183.
53. Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
54. The Seebach group has been a pioneer in the field of chiral imidazolidinones; see: Naef, R.; Seebach, D. Helv. Chim. Acta 1985, 68, 135.
55. Mayr, H.; Ofial, A. R.; Würthwein, E.-U.; Aust, N. C. J. Am. Chem. Soc. 1997, 119, 12727.
56. Marigo, M.; Wabnitz, T. C; Fielenbach, D.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794.
57. Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212.
58. Erkkilä, A.; Pihko, P. M.; Clarke, M.-R. Adv. Synth. Catal. 2007, 349, 802.
59. Sakakura, A.; Suzuki, K.; Nakano, K.; Ishihara, K. Org. Lett. 2006, 8, 2229.
60. Sakakura, A.; Suzuki, K.; Ishihara, K. Adv. Synth. Catal. 2006, 348, 2457.
61. Ishihara, K.; Nakano, K. J. Am. Chem. Soc. 2005, 127, 10504.
62. Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193.
63. Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368.
64. Shriver, J.; Abrahamson, E. W.; Mateescu, G. D. J. Am. Chem. Soc. 1976, 98, 2407.
65. Santarsiero, B. D.; James, M. N. G.; Mahendran, M.; Childs, R. F. J. Am. Chem. Soc. 1990, 112, 9416.
66. Elia, G. R.; Childs, R. F.; Britten, J. F.; Yang, D.S. C.; Santarsiero, B. D. Can. J. Chem. 1996, 74, 591.
67. Buda, F.; Giannozzi, P.; Mauri, F. J. Phys. Chem. B 2000, 104, 9048.
68. Childs, R. F.; Dickie, B. D. J. Am. Chem. Soc. 1983, 105, 5041.
69. Pankratz, M.; Childs, R. F. J. Org. Chem. 1985, 50, 4553.
70. Childs, R. F.; Dickie, B. D.; Faggiani, R.; Fyfe, C. A.; Lock, C. J. L.; Wasylishen, R. E. J. Crystallogr. Spectrosc. Res. 1985, 15, 73.
71. Childs, R. F.; Shaw, G. S.; Lock, C. J. L. J. Am. Chem. Soc. 1989, 111, 5424.
72. Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801.
73. Lemay, M.; Aumand, L.; Ogilvie, W. W. Adv. Synth. Catal. 2007, 349, 441.
74. Kolehmeinen, E.; Laihia, K.; Mänttäri, P. Magn. Reson. Chem. 1991, 29, 1109.
75. Jung, M. E.; Vaccaro, W. D.; Buszek, K. R. Tetrahedron Lett. 1989, 30, 1893.
76. Griesbeck, A. G. J. Org. Chem. 1989, 54, 4981.
77. Baldwin, J. E.; Chesworth, R.; Parker, J. S.; Russell, A. T. Tetrahedron Lett. 1995, 36, 9551.
78. (a) Tchabanenko, K.; Adlington, R. M.; Cowley, A. R.; Baldwin, J. E. Org. Lett. 2005, 7, 585.
79. (b) Tchabanenko, K.; Chesworth, R.; Parker, J. S.; Anand, N. K.; Russell, A. T.; Adlington, R. M.; Baldwin, J. E. Tetrahedron 2005, 61, 11649.
80. Allemann, C.; Gordillo, R.; Clemente, F. R.; Cheong, P. H.-Y.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558.
81. Gordillo, R.; Houk, K. N. J. Am. Chem. Soc. 2006, 128, 3543.
82. Benaglia, M.; Celentano, G.; Cinquini, M.; Puglisi, A.; Cozzi, F. Adv. Synth. Catal. 2002, 344, 149.
83. Puglisi, A.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Celentano, G. Eur. J. Org. Chem. 2004, 567.
84. Selkälä, S. A.; Tois, J.; Pihko, P. M.; Koskinen, A. M. P. Adv. Synth. Catal. 2002, 344, 941.
85. Park, J. K.; Sreekanth, P.; Kim, B. M. Adv. Synth. Catal. 2004, 346, 49.
86. Chu, Q.; Zhang, W.; Curran, D. P. Tetrahedron Lett. 2006, 47, 9287.
87. Pecinovsky, C. S.; Nicodemus, G. D.; Gin, D. L. Chem. Mater. 2005, 17, 4889.
88. Gin, D. L.; Lu, X.; Nemade, P. R.; Pecinovsky, C. S.; Xu, Y.; Zhou, M. Adv. Funct. Mater. 2006, 16, 865.
89. Zhang, Y.; Zhao, L.; Lee, S. S.; Ying, J. Y. Adv. Synth. Catal. 2006, 348, 2027.
90. Liang, C. O.; Fréchet, J. M. J. Macromolecules 2005, 38, 6276.
91. Cavill, J. L.; Peters, J.-U.; Tomkinson, N. C. O. Chem. Commun. 2003, 728.
92. Cavill, J. L.; Elliott, R. L.; Evans, G.; Jones, I. L.; Platts, J. A.; Ruda, A. M.; Tomkinson, N. C. O. Tetrahedron 2006, 62, 410.
93. Evans, G. J. S.; White, K.; Platts, J. A.; Tomkinson, N. C. O. Org. Biomol. Chem. 2006, 4, 2616.
94. Fina, N. J.; Edwards, J. O. Int. J. Chem. Kinet. 1973, 5, 1.
95. See ref 44: Table 1, entry 5.
96. Lemay, M.; Ogilvie, W. W. Org. Lett. 2005, 7, 4141.
97. Lemay, M.; Ogilvie, W. W. J. Org. Chem. 2006, 71, 4663.
98. Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
99. Kano, T.; Tanaka, Y.; Maruoka, K. Org. Lett. 2006, 8, 2687.
100. Bonini, B. F.; Capitò, E.; Comes-Franchini, M.; Fochi, M.; Ricci, A.; Zwanenburg, B. Tetrahedron: Asymmetry 2006, 17, 3135.
101. Mossé, S.; Alexakis, A. Org. Lett. 2006, 8, 3577.
102. Kim, K. H.; Lee, S.; Lee, D.-W.; Ko, D.-H.; Ha, D.-C. Tetrahedron Lett. 2005, 46, 5991.
103. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
104. Selkälä, S. A.; Koskinen, A. M. P. Eur. J. Org. Chem. 2005, 1620.
105. Wilson, R. M.; Jen, W. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 11616.
106. de Figueiredo, R. M.; Berner, R.; Julis, J.; Liu, T.; Türp, D.; Christmann, M. J. Org. Chem. 2007, 72, 640.
107. Kunz, R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
108. Wipf, P.; Wang, X. Tetrahedron Lett. 2000, 41, 8747.
109. Kinsman, A. C.; Kerr, M. A. J. Am. Chem. Soc. 2003, 125, 14120.
110. Lambert, T. H.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 426.
111. de Figuieredo, R. M.; Voith, M.; Fröhlich, R.; Christmann, M. Synlett 2007, 391 .
112. Tiefenbacher, K.; Arion, V. B.; Mulzer, J. Angew. Chem. Int. Ed. 2007, 46, 2690.
113. Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
114. Chow, S. S.; Nevalainen, M.; Evans, C. A.; Johannes, C. W. Tetrahedron Lett. 2007, 48, 277.
115. Karlsson, S.; Högberg, H.-E. Tetrahedron: Asymmetry 2002, 13, 923.
116. Karlsson, S.; Högberg, H.-E.; Eur. J. Org. Chem. 2003, 2782.
117. Chen, W.; Yuan, X.-H.; Li, R.; Du, W.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Adv. Synth. Catal. 2006, 348, 1818.
118. Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176.
119. Kawara, A.; Taguchi, T. Tetrahedron Lett. 1994, 35, 8805.
120. Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520.
121. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
122. Knudsen, K. R.; Mitchell, C. E. T.; Ley, S. V. Chem. Commun. 2006, 66.
123. For example, see: (a) Hartikka, A.; Arvidsson, P. I. Tetrahedron: Asymmetry 2004, 15, 1831.
124. (b) Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Catal. 2005, 3, 84.
125. Mitchell, C. E. T.; Brenner, S. E.; Ley, S. V. Chem. Commun. 2005, 5346.
126. Brandau, S.; Landa, A.; Franzén, J.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 4305.
127. Bui, T.; Barbas, C. F., III Tetrahedron Lett. 2000, 41, 6951.
128. Cravotto, G.; Nano, G. M.; Tagliapietra, S. Synthesis 2001, 49.
129. Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955.
130. Kim, H.; Yen, C.; Preston, P.; Chin, J. Org. Lett. 2006, 8, 5239.
131. Halland, N.; Jørgensen, K. A.; Hansen, T. PCT Int. Appl. 2003 WO03/ 050105.
132. Xie, J.-W.; Yue, L.; Chen, W.; Du, W.; Zhu, J.; Deng, J.-G.; Chen, Y.-C. Org. Lett. 2007, 9, 413.
133. Xie, J.-W.; Chen, W.; Li, R.; Zeng, M.; Du, W.; Yue, L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Angew. Chem., Int. Ed. 2007, 46, 389.
134. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
135. Pulkkinen, J.; Aburel, P. S.; Halland, N. Jorgensen, K. A. Adv. Synth. Catal. 2004, 346, 1077.
136. Gryko, D. Tetrahedron: Asymmetry 2005, 16, 1377.
137. Marigo, M.; Bertelsen, S.; Landa, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 5475.
138. Carlone, A.; Marigo, M.; North, C.; Landa, A.; Jørgensen, K. A. Chem. Commun. 2006, 4928.
139. McMurry, J. E.; Melton, J. J. Am. Chem. Soc. 1971, 93, 5309.
140. Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Orlova, S. A.; Kuz'mina, N. A.; Bodrov, D. E. Russ. Chem. Bull. 1993, 42, 1525.
141. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233.
142. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223.
143. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975.
144. Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331.
145. Prieto, A.; Halland, N.; Jørgensen, K. A. Org. Lett. 2005, 7, 3897.
146. Mitchell, C. E. T.; Brenner, S. E.; García-Fortanet, J.; Ley, S. V. Org. Biomol. Chem. 2006, 4, 2039.
147. Tsogoeva, S. B.; Jagtap, S. B.; Ardemasova, Z. A.; Kalikbevich, V. N. Eur. J. Org. Chem. 2004, 4014.
148. Tsogoeva, S. B.; Jagtap, S.B. Synlett 2004, 2624.
149. Tsogoeva, S. B.; Jagtap, S. B.; Ardemasova, Z. A. Tetrahedron: Asymmetry 2006, 17, 989.
150. Hanessian, S.; Shao, Z.; Warrier, J. S. Org. Lett. 2006, 8, 4787.
151. Hojabri, L.; Hartikka, A.; Moghaddam, F. M.; Arvidsson, P. I. Adv. Synth. Catal. 2007, 349, 740.
152. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
153. Breistein, P.; Karlsson, S.; Hedenström, E. Tetrahedron: Asymmetry 2006, 17, 107.
154. Banwell, M. G.; Beek, D. A. S.; Smith, J. A. Org. Biomol. Chem. 2004, 2, 157.
155. Banwell, M. G.; Beck, D. A. S.; Willis, A. C. Arkivoc 2006, 163.
156. Austin, J. F.; Kim, S.-G.; Sinz, C. J.; Xiao, W.-J.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. 2004, 101, 5482.
157. Gordillo, R.; Carter, J.; Houk, K. N. Adv. Synth. Catal. 2004, 346, 1175.
158. Denhart, D. J.; Mattson, R. J.; Ditta, J. L.; Macor, J. E. Tetrahedron Lett. 2004, 45, 3803.
159. King, H. D.; Meng, Z.; Denhart, D.; Mattson, R.; Kimura, R.; Wu, D.; Gao, Q.; Macor, J, E. Org. Lett. 2005, 7, 3437.
160. Gerasyuto, A. I.; Hsung, R. P.; Sydorenko, N.; Slafer, B. J. Org. Chem. 2005, 70, 4248.
161. Li, D.-P.; Guo, Y.-C.; Ding, Y.; Xiao, W.-J. Chem. Commun. 2006, 799.
162. Chen, W.; Du, W.; Yue, L.; Li, R.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Org. Biomol. Chem. 2007, 5, 816.
163. Bartoli, G.; Bosco, M.; Carlone, A.; Pesciaioli, F.; Sambri, L.; Melchiorre, P. Org. Lett. 2007, 9, 1403.
164. Brown, S. P. Doctoral Dissertation, California Institute of Technology, Pasadena, CA, 2005.
165. Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
166. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
167. Kim, S.-G.; Kim, J.; Jung, H. Tetrahedron Lett. 2005, 46, 2437.
168. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
169. Robichaud, J.; Tremblay, F. Org. Lett. 2006, 8, 597.
170. Wang, W.; Li, H.; Wang, J. Org. Lett. 2005, 7, 1637.
171. Xie, J.-W.; Yue, L.; Xue, D.; Ma, X.-L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Chem. Commun. 2006, 1563.
172. Gotoh, H.; Masui, R.; Ogino, H.; Shoji, M.; Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 6853.
173. Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 6660.
174. Yang, J. W.; Hechavarria Fonseca, M. T.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2005, 44, 108.
175. Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32.
176. Zhao, G.-L.; Córdova, A. Tetrahedron Lett. 2006, 47, 7417.
177. Tuttle, J. B.; Ouellet, S. G.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 12662.
178. Marigo, M.; Schulte, T.; Franzén, J.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710.
179. Brandau, S.; Maerten, E.; Jorgensen, K. A. J. Am. Chem. Soc. 2006, 128, 14986.
180. Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354.
181. Rios, R.; Sundén, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Córdova, A. Tetrahedron Lett. 2006, 47, 8547.
182. Rios, R.; Sundén, H.; Ibrahem, I.; Zhao, G.-L.; Córdova, A. Tetrahedron Lett. 2006, 47, 8679.
183. Takasu, K.; Maiti, S.; Ihara, M. Heterocycles 2003, 59, 51.
184. Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962.
185. Sundén, H.; Ibrahem, I.; Eriksson, L.; Córdova, A. Angew. Chem., Int. Ed. 2005, 44, 4877.
186. Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328.
187. Vesley, J.; Ibrahem, I.; Rios, R.; Zhao, G.-L.; Xu, Y.; Córdova, A. Tetrahedron Lett. 2007, 48, 2193.
188. Dinér, P.; Nielsen, M.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983.
189. Uria, U.; Vicario, J. L.; Badía, D.; Carrillo, L. Chem. Commun. 2007, 2509.
190. Ibrahem, I.; Rios, R.; Vesley, J.; Zhao, G.-L.; Córdova, A. Chem. Commun. 2007, 849.
191. Brossmer, C.; Arntz, D. Process for the production of 1,3-propanediol. Ger. Patent 19703383, 1997.
192. Brossmer, C.; Arntz, D. Process for preparing 3-hydroxyalkanals. Ger. Patent 19705714, 1997.
193. Kano, T.; Tanaka, Y.; Maruoka, K. Tetrahedron Lett. 2006, 47, 3039.
194. Ramachary, D. B.; Mondal, R. Tetrahedron Lett. 2006, 47, 7689.
195. Bertelsen, S.; Dinér, P.; Johansen, R. L.; Jørgensen, K. A. J. Am. Chem. Soc. 2007, 129, 1536.
196. Sundén, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Córdova, A. Chem.-Eur. J. 2007, 13, 574.
197. Govender, T.; Hojabri, L.; Moghaddam, F. M.; Arvidsson, P. I. Tetrahedron: Asymmetry 2006, 17, 1763.
198. Li, H.; Wang, J.; E-Nunu, T.; Zu, L.; Jiang, W.; Wei, S.; Wang, W. Chem. Commun. 2007, 507.
199. Rios, R.; Sundén, H.; Ibrahem, I.; Córdova, A. Tetrahedron Lett. 2007, 48, 2181.
200. Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151.
201. Peelen, T. J.; Chi, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11598.
202. Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958.
203. Mangion, I. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3696.
204. Hayashi, Y.; Gotoh, H.; Tamura, T.; Yamaguchi, H.; Masui, R.; Shoji, M. J. Am. Chem. Soc. 2005, 127, 16028.
205. Chen, S.-H.; Hong, B.-C.; Su, C.-F.; Sarshar, S. Tetrahedron Lett. 2005, 46, 8899.
206. Bertelsen, S.; Marigo, M.; Brandes, S.; Dinér, P.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 12973.
207. Utsumi, N.; Zhang, H.; Tanaka, F.; Barbas, C. F., III Angew. Chem., Int. Ed. 2007, 46, 1878.
208. For an excellent overview of the field of domino reactions, see: Tietze, L. F.; Brasche, G.; Gericke, K. M. Domino Reaction in Organic Synthesis; Wiley: Weinheim, Germany, 2006.
209. Hansen, H. M.; Longbottom, D. A.; Ley, S. V. Chem. Commun. 2006, 4838.
210. Marigo, M.; Franzén, J.; Poulsen, T. B.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6964.
211. Zhuang, W.; Marigo, M.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 3883.
212. Sundén, H.; Ibrahem, I.; Córdova, A. Tetrahedron Lett. 2006, 47, 99.
213. Lee, S.; MacMillan, D. W. C. Tetrahedron 2006, 62, 11413.
214. Lattanzi, A. Org. Lett. 2005, 7, 2579.
215. Lattanzi, A. Adv. Synth. Catal. 2006, 348, 339.
216. Lattanzi, A.; Russo, A. Tetrahedron 2006, 62, 12264.
217. Liu, X.-Y.; Li, Y.-W.; Wang, G.-Y.; Chai, Z.; Wu, Y.-Y.; Zhao, G. Tetrahedron: Asymmetry 2006, 17, 750.
218. Li, Y.; Liu, X.; Yang, Y.; Zhao, G. J. Org. Chem. 2007, 72, 288.
219. List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395.
220. Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12, 63.
221. Vesley, J.; Ibrahem, I.; Zhao, G.-L.; Rios, R.; Córdova, A. Angew. Chem., Int. Ed. 2007, 46, 778.
222. Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. J. Am. Chem. Soc. 2005, 127, 15036.
223. Li, H.; Zu, L.; Xie, H.; Wang, J.; Jiang, W.; Wang, W. Org. Lett. 2007, 9, 1833.
224. Asato, A. E.; Watanabe, C.; Li, X.-Y.; Liu, R. S. H. Tetrahedron Lett. 1992, 33, 3105.
225. Bench, B. J.; Liu, C.; Evett, C. R.; Watanabe, C. M. H. J. Org. Chem. 2006, 71, 9458.
226. Rajagopal, D.; Narayanan, R.; Swaminathan, S. Tetrahedron Lett. 2001, 42, 4887.
227. Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F. Tetrahedron Lett. 2002, 43, 6743.
228. Thayumanavan, R.; Dhevalapally, B.; Sakthivel, K.; Tanaka, F.; Barbas, C. F. Tetrahedron Lett. 2002, 43, 3817.
229. Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F. Angew. Chem., Int. Ed. 2003, 42, 4233.
230. Ramachary, D. B.; Anebouselvy, K.; Chowdari, N. S.; Barbas, C. F. J. Org. Chem. 2004, 69, 5838.
231. Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F. Synlett 2003, 1910.
232. Ramachary, D. B.; Barbas, C. F. Chem.-Eur. J. 2004, 10, 5323.
233. Enders, D.; Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861.
234. Enders, D.; Hüttl, M. R. M.; Runsink, J.; Raabe, G.; Wendt, B. Angew. Chem., Int. Ed. 2007, 46, 467.
235. Hong, B.-C.; Nimje, R. Y.; Yang, C.-Y. Tetrahedron Lett. 2007, 48, 1121.
236. Hong, B.-C.; Tseng, H.-C.; Chen, S.-H. Tetrahedron 2007, 63, 2840.
237. Hong, B.-C.; Wu, M.-F.; Tseng, H.-C.; Liao, J.-H.; Org. Lett. 2006, 8, 2217.
238. Carlone, A.; Cabrera, S.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1101.
239. Itoh, T.; Yokoya, M.; Miyauchi, K.; Nagata, K.; Ohsawa, A. Org. Lett. 2003, 5, 4301.
240. Itoh, T.; Yokoya, M.; Miyauchi, K.; Nagata, K.; Ohsawa, A. Org. Lett. 2006, 8, 1533.
241. Balailae, S.; Bararjanian, M.; Amani, A. M.; Movassagh, B. Synlett 2006, 263.
242. Li, H.; Wang, J.; Xie, H.; Zu, L.; Jiang, W.; Duesler, E. N.; Wang, W. Org. Lett. 2007, 9, 965.
243. Aznar, F.; García, A.-B.; Cabal, M.-P. Adv. Synth. Catal. 2006, 348, 2443.
244. Kumar, A.; Maurya, R. A. Tetrahedron 2007, 63, 1946.
245. Harmata, M.; Ghosh, S. K.; Hong, X.; Wacharasindhu, S.; Kirchhoefer, P. J. Am. Chem. Soc. 2003, 125, 2058.
246. Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizume, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435.
247. Sundén, H.; Dahlin, N.; Ibrahem, I.; Adolfsson, H.; Córdova, A. Tetrahedron Lett. 2005, 46, 3385.
248. Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. Tetrahedron Lett. 2001, 42, 4441.
249. List, B.; Castello, C. Synlett 2001, 1687.
250. Córdova, A.; Notz, W.; Barbas, C. F. J. Org. Chem. 2002, 67, 301.
251. Nakamura, N.; Yamamoto, H. Chem. Commun. 2002, 1648.
252. Dirksen, A.; Hackeng, T. M.; Dawson, P. E. Angew. Chem., Int. Ed. 2006, 45, 7581.
253. Dirksen, A.; Dirksen, S.; Hackeng, T. M.; Dawson, P. E. J. Am. Chem. Soc. 2006, 128, 15602.
254. Knoevenagel, E. Chem. Ber. 1898, 29, 172.
255. Knoevenagel, E. Chem. Ber. 1898, 31, 2585.
256. Jones, G. Org. React. 1967, 15, 204.
257. Song, A.; Wang, X.; Lam, K. S. Tetrahedron Lett. 2003, 44, 1755.
258. Watson, B. T.; Christiansen, G. E. Tetrahedron Lett. 1998, 39, 6087.
259. Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Synth. Commun. 2003, 33, 1587.
260. Dutov, M. D.; Serushkina, O. V.; Shevelev, S. A. Mendeleev Commun. 2002, 17.
261. Inokuchi, T.; Kawafuchi, H. J. Org. Chem. 2006, 71, 947.
262. Tanikaga, R.; Konya, N.; Hamamura, K.; Kaji, A. Bull. Chem. Soc. Jpn. 1988, 61, 3211.
263. See also: Tnikaga, R.; Konya, N.; Tamura, T.; Kaji, A. Chem. Soc., Perkin Trans. 1 1987, 825.
264. Wang, Y.; Shang, Z.-C.; Wu, T.-X.; Fan, J.-C.; Chen, X. J. Mol. Catal., A 2006, 253, 212.
265. Biaggi, B.; Benaglia, M.; Raimondi, L.; Cozzi, F. Tetrahedron 2006, 62, 12375.
266. Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137.
267. Demicheli, G.; Maggi, R.; Mazzacani, A.; Righi, P.; Sartori, G.; Bigi, F. Tetrahedron Lett. 2001, 42, 2401.
268. See also: Angeletti, E.; Canepa, C.; Martinetti, G.; Venturello, P. Tetrahedron Lett. 1988, 29, 2261.
269. Wang, X.; Lin, K. S. K.; Chan, J. C. C.; Cheng, S. J. Phys. Chem. B 2005, 109, 1763.
270. Isobe, K.; Hoshi, T.; Suzuki, T.; Hagiwara, H. Mol. Diversity 2005, 9, 317.
271. Rajender Reddy, K.; Rajgopal, K.; Uma, Maheswari, C.; Lakshmi Kantam, M. New J. Chem. 2006, 30, 1549.
272. Tamami, B.; Fadavi, A. Iran. Polym. J. 2006, 15, 331.
273. Simpson, J.; Rathbone, D. L.; Billington, D. C. Tetrahedron Lett. 1999, 40, 7031.
274. Macquarrie, D. J.; Jackson, D. B.; Tailland, S.; Utting, K. A. J. Mater. Chem. 2001, 11, 1843.
275. Al-Haq, N.; Ramnauth, R.; Kleinebiekel, S.; On, D. L.; Sullivan, A. C.; Wilson, J. Green Chem. 2002, 4, 239.
276. Wirz, R.; Ferri, D.; Baiker, A. Langmuir 2006, 22, 3698.
277. Bass, J. D.; Solovyov, A.; Pascall, A. J.; Katz, A. J. Am. Chem. Soc. 2006, 128, 3737.
278. Miao, W.; Chan, T. H. Acc. Chem. Res. 2006, 39, 897.
279. Zhang, L.; Rana, T. M. J. Comb. Chem. 2004, 6, 457.
280. Guo, H.; Arvanitis, E. A.; Pottorf, R. S.; Player, M. R. J. Comb. Chem. 2003, 5, 408.
281. Peng, Y.; Song, G. Green Chem. 2003, 5, 704.
282. Correa, W. H.; Edwards, J. K.; McCluskey, A.; McKinnon, I.; Scott, J. L. Green Chem. 2003, 5, 30.
283. Ramachary, D. B.; Ramakumar, K.; Kishor, M. Tetrahedron Lett. 2005, 46, 7037.
284. Baidossi, M.; Joshi, A. V.; Mukhopadhyay, S.; Sasson, Y. Tetrahedron Lett. 2005, 46, 1885.
285. Ramachary, D. B.; Kishor, M.; Reddy, G. B. Org. Biomol. Chem. 2006, 4, 1641.
286. Ramachary, D. B.; Reddy, G. B. Org. Biomol. Chem. 2006, 4, 4463.
287. Ramachary, D. B.; Ramakumar, K.; Narayana, V. V. J. Org. Chem. 2007, 72, 1458.
288. (a) Lim, N. C.; Schuster, J. V.; Porto, M. C.; Tanudra, M. A.; Yao, L.; Freake, H. C.; Bruckner, C. Inorg. Chem. 2005, 44, 2018.
289. (b) Frédérick, R.; Robert, S.; Charlier, C.; de Ruyck, J.; Wouters, J.; Priotte, B.; Masereel, B.; Pochet, L. J. Med. Chem. 2005, 48, 7592.
290. Reddy, N. S.; Mallireddigari, M. R.; Cosenza, S.; Gumireddy, K.; Bell, S. C.; Reddy, P.; Reddy, M. V. R. Bioorg. Med. Chem. Lett. 2004, 14, 4093.
291. Snider, B. B.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 549.
292. Kar, A.; Gogoi, S.; Argade, N. P. Tetrahedron 2005, 61, 5297.
293. Chérouvier, J. R.; Boissel, J.; Carreaux, F.; Bazureau, J. P. Green Chem. 2001, 3, 165.
294. Unangst, P. C.; Connor, D. T.; Cetenko, W. A.; Sorenson, R. J.; Kosdan, C. R.; Sircar, J. C.; Wright, C. D.; Schrier, D. J.; Dyer, R. D. J. Med. Chem. 1994, 37, 322.
295. Milhazes, N.; Cunha-Oliveira, T.; Martins, P.; Carrido, J.; Oliveira, C.; Rego, A. C.; Borges, F. Chem. Res. Tox. 2006, 19, 1294.
296. Flipo, M.; Beghyn, T.; Leroux, V.; Florent, I.; Deprez, B. P.; Deprez-Poulain, R. F. J. Med. Chem. 2007, 50, 1322.
297. Larsen, S. D.; Barf, T.; Liljebris, C.; May, P. D.; Ogg, D.; O'Sullivan, T. J.; Palazuk, B. J.; Schostarez, H. J.; Stevens, F. C.; Bleasdale, J. E. J. Med. Chem. 2002, 45, 598.
298. Liu, G.; Link, J. T.; Pei, Z.; Reilly, E. B.; Leitza, S.; Nguyen, B.; Marsh, K. C.; Okasinski, G. F.; von Geldern, T. W.; Ormes, M.; Fowler, K.; Gallatin, M. J. Med. Chem. 2000, 43, 4025.
299. Fors, K. S.; Gage, J. R.; Heier, R. F.; Kelly, R. C.; Perrault, W. R.; Wicnienski, N. J. Org. Chem. 1998, 63, 7348.
300. (a) Cregge, R. J.; Farr, R. A.; Friedrich, D.; Hulshof, J.; Janowick, D. A.; Meikrantz, S.; Metz, W. A. Tetrahedron Lett. 2001, 42, 1407.
301. (b) Baron, B. M.; Cregge, R. J.; Farr, R. A.; Friedrich, D.; Gross, R. S.; Harrison, B. L.; Janowck, D. A.; Matthews, D.; McCloskey, T. C.; Meikrantz, S.; Nyce, P. L.; Vaz, R.; Metz, W. A J. Med. Chem. 2005, 48, 995.
302. Huang, C.-H.; McClenaghan, N. D.; Kuhn, A.; Hofstraat, J. W.; Bassani, D. M. Org. Lett. 2005, 7, 3409.
303. Tietze, L. F.; Rackelmann, N.; Müller, I. Chem. - Eur. J. 2004, 10, 2722.
304. For a review, see: Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304.
305. Mannich, C. Arch. Pharm. 1912, 250, 647.
306. Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2., p 893.
307. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 133.
308. (a) Shirai, M.; Yoshida, Y.; Furuya, T.; Sadaike, S. JP2006045160, 2006.
309. (b) Deshpande, R. M.; Diwakar, M. M.; Chaudhari, R. V. W02005063668A1, 2005.
310. (c) Deshpande, R. M.; Diwakar, M. M.; Mahajan, A. N.; Chaudhari, R. V. J. Mol. Catal., A. 2004, 211, 49.
311. (d) Hong, Y.-S.; Chang, F. J.; Lu, L.; Lin, W.-C. Tetrahedron 1998, 54, 5233.
312. (e) Matsuoka, K. JP04173757, 1992.
313. (f) Nagareda, K.;Yoshimura, N. JP 06263683, 1994; JP3324820, 2002.
314. (g) Duembgen,G.; Fouquet, G.; Krabetz, R.; Lucas, E.; Merger, F.; Nees, F. EP0092097A1, 1983.
315. (h) Duembge, G.; Fouquet, G.; Krabetz, R.; Lucas, E.; Merger, F.; Nees, F. DE3213681, 1983.
316. (i) Merger, F.;Förster, H. J. EP58927, 1982.
317. (j) Bernhagen, W.; Bach, H.; Brundin, E.; Gick, W., Springer, H.; Hack, A. DE285504,1980. For examples of stoichiometric Mannich α-methylenations, see:
318. (k) Marvel, C.S.; Myers, R. L.; Saunders, J. H. J. Am. Chem. Soc. 1948, 70, 1694.
319. (l) Snider, B. B.; Lobera, M.; Marien, T. P. J. Org. Chem. 2003, 68, 6451.
320. (m) Basu, K.; Richards, J.; Paquette, L. A. Synthesis 2004, 2841.
321. (a) Yoshida, K.; Grieco, P. J. Org. Chem. 1984, 49, 5257.
322. (b)Heckendorn, R.; Allgeier, H.; Baud, J.; Gunzenhauser, W.; Angst, C. J. Med. Chem. 1993, 36, 3721.
323. Ishikawa, T.; Uedo, E.; Okada, S.; Saito, S. Synlett 1999, 450.
324. Erkkilä, A.; Pihko, P. M. J. Org. Chem. 2006, 71, 2538.
325. Recently, additional kinetic evidence for the proposed double activation mechanism (iminium for the acceptor, enamine for donor) has been presented in a full account of this work: Erkkilä, A.; Pihko, P. M. Eur. J. Org. Chem. 2007, 4205.
326. Guthrie, J. P.; Jordan, F. J. Am. Chem. Soc. 1972, 94, 9136.
327. Ogino, K.; Tamiya, H:, Kimura, Y.; Azuma, H.; Tagaki, W. J. Chem. Soc., Perkin Trans. 2 1996, 979.
328. Wald, G. The Molecular Basis of Visual Excitation in Nobel Lectures, Physiology or Medicine 1963-1970; Elsevier Publishing Company: Amsterdam, The Netherlands, 1972; p 292.
329. Brogan, A. P.; Dickerson, T. J.; Boldt, G. E.; Janda, K. D. Proc. Matl. Acad. Sci. 2005, 102, 10433.