Chiral phosphoric acid-catalyzed enantioselective three-component Povarov reaction using enecarbamates as dienophiles: Highly diastereo- and enantioselective synthesis of substituted 4-aminotetrahydroquinolines

Journal of the American Chemical Society

Volumn 133, Issue 37, 2011, Pages 14804-14813

  Dagousset, Guillaume ^a   Zhu, Jieping ^b   Masson, Géraldine ^a  

^a CNRS   (France)

^b EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALDEHYDES; CATALYST LOADINGS; CATALYTIC SPECIES; DIASTEREO- AND ENANTIOSELECTIVITY; DIASTEREOSELECTIVITIES; DIENOPHILES; ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; HIGH YIELD; LINEAR CORRELATION; MECHANISTIC STUDIES; STEREOGENIC CENTERS; THREE-COMPONENT;

ALDEHYDES; ANILINE; CATALYSIS; CATALYSTS; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; PHOSPHORIC ACID;

SYNTHESIS (CHEMICAL);

4 AMINOTETRAHYDROQUINOLINE; ALDEHYDE; ANILINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; PHOSPHORIC ACID; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; ELECTRON TRANSPORT; ENANTIOMER; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE; POVAROV REACTION; SYNTHESIS;

CARBAMATES; CATALYSIS; PHOSPHORIC ACIDS; QUINOLINES; STEREOISOMERISM;

EID: 80052815341     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205891m     Document Type: Article

References (145)

1. Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031
2. Omura, S.; Nakagawa, A.; Hashimoto, H.; Oiwa, R.; Iwai, Y.; Hirano, A.; Shibukawa, N.; Kojima, Y. J. Antibiot. 1980, 33, 1395
3. Copp, B. R.; Fulton, K. F.; Perry, N. B.; Blunt, J. W.; Munro, M. H. G. J. Org. Chem. 1994, 59, 8233
4. Jacquemond-Collet, I.; Benoit-Vical, F.; Mustofa; Valentin, A.; Stanislas, E.; Mallié, M.; Fourasté, I. Planta Med. 2002, 68, 68
5. Wallace, O. B.; Lauwers, K. S.; Jones, S. A.; Dodge, J. A. Bioorg. Med. Chem. Lett. 2003, 13, 1907
6. Di Fabio, R.; Tranquillini, E.; Bertani, B.; Alvaro, G.; Micheli, F.; Sabbatini, F.; Pizzi, M. D.; Pentassuglia, G.; Pasquarello, A.; Messeri, T.; Donati, D.; Ratti, E.; Arban, R.; Dal Forno, G.; Reggiani, A.; Barnaby, R. J. Bioorg. Med. Chem. Lett. 2003, 13, 3863
7. Avemaria, F.; Vanderheiden, S.; Bräse, S. Tetrahedron 2003, 59, 6785
8. Morita, H.; Hirasawa, Y.; Shinzato, T.; Kobayashi, J. Tetrahedron 2004, 60, 7015
9. Asolkar, R. N.; Schroeder, D.; Heckmann, R.; Lang, S.; Wagner-Doebler, I.; Laatsch, H. J. Antibiot. 2004, 57, 17
10. Shigeyama, T; Katakawa, K.; Kogure, N.; Kitajima, M.; Takayama, H. Org. Lett. 2007, 9, 4069
11. Morehouse, L. A.; Sugarman, E. D.; Bourassa, P.-A.; Sang, T. M.; Zimetti, F.; Gao, F.; Rothblat, G. H.; Milici, A. J. J. Lipid Res. 2007, 48, 1263
12. Rano, T. A.; McMaster, E. S.; Pelton, P. D.; Yang, M.; Demarest, K. T.; Kuo, G. H. Bioorg. Med. Chem. Lett. 2009, 19, 2456
13. Kumar, A.; Srivastava, S.; Gupta, G.; Chaturvedi, V.; Sinha, S.; Srivastava, R. ACS Comb. Sci. 2011, 13, 65
14. Paris, D.; Cottin, M.; Demonchaux, P.; Augert, G.; Dupassieux, P.; Lenoir, P.; Peck, M. J.; Jasserand, D. J. Med. Chem. 1995, 38, 669
15. Xia, Y.; Yang, Z.-Y.; Xia, P.; Bastow, K. F.; Tachibana, Y.; Kuo, S.-C.; Hamel, E.; Hackl, T.; Lee, K.-H. J. Med. Chem. 1998, 41, 1155
16. Hanada, K.; Furuya, K.; Inoguchi, K.; Miyakawa, M.; Nagata, N. Int. Patent WO 0127086, 2001
17. Chem. Abstr. 2001, 134, 295752.
18. Bazin, M.; Kuhn, C. J. Comb. Chem. 2005, 7, 302 and references therein
19. Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215
20. Xia, C.; Heng, L.; Ma, D. Tetrahedron Lett. 2002, 43, 9405
21. Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913
22. Damon, D. B.; Dugger, R. W. Eur. Pat. Appl. EP1125929, 2001, and U.S. Patent 6,313,142, 2001.
23. Damon, D. B.; Dugger, R. W.; Scott, R. W. U.S. Patent 6,689,897, 2004.
24. Damon, D. B.; Dugger, R. W.; Magnus-Aryitey, G.; Ruggeri, R. B.; Wester, R. T.; Tu, M.; Abramov, Y. Org. Process Res. Dev. 2006, 10, 464
25. Damon, D. B.; Dugger, R. W.; Hubbs, S. E.; Scott, J. M.; Scott, R. W. Org. Process Res. Dev. 2006, 10, 472
26. Leeson, P. D.; Carling, R. W.; Moore, K. W.; Moseley, A. M.; Smith, J. D.; Stevenson, G.; Chan, T.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R.; Hoogsteen, K. J. Med. Chem. 1992, 35, 1954
27. Carling, R. W.; Leeson, P. D.; Moseley, A. M.; Smith, J. D.; Saywell, K.; Tricklebank, M. D.; Kemp, J. A.; Marshall, G. R.; Foster, A. C.; Grimwood, S. Bioorg. Med. Chem. Lett. 1993, 3, 65
28. Murarka, S.; Deb, I.; Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 13226
29. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847
30. Cao, W.; Liu, X.; Wang, W.; Lin, L.; Feng, X. Org. Lett. 2011, 13, 600
31. Zhou, G.; Liu, F.; Zhang, J. Chem. Eur. J. 2011, 17, 3101
32. Mori, K.; Ehara, K.; Kurihara, K.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 6166
33. Deport, C.; Buchotte, M.; Abecassis, K.; Tadaoka, H.; Ayad, T.; Ohshima, T.; Genet, J.-P.; Mashima, K.; Ratovelomanana-Vidal, V. Synlett 2007, 2743
34. Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536
35. Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683
36. Guo, Q.-S.; Du, D.-M.; Xu, J. Angew. Chem., Int. Ed. 2008, 47, 759
37. Dobereiner, G. E.; Nova, A.; Schley, N. D.; Hazari, N.; Miller, S. J.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2011, 133, 7547
38. Wang, T.; Zhuo, L.-G.; Li, Z.; Chen, F.; Ding, Z.; He, Y.; Fan, Q.-H.; Xiang, J.; Yu, Z.-X.; Chan, A. S. C. J. Am. Chem. Soc. 2011, 133, 9878
39. Guin, M.; Phua, P. H.; Caille, J.-C.; Hii, K. K. J. Org. Chem. 2007, 72, 6290
40. Davies, S. G.; Mujtaba, N.; Roberts, P. M.; Smith, A. D.; Thomson, J. E. Org. Lett. 2009, 11, 1959
41. Jia, Z.-X.; Luo, Y.-C.; Xu, P.-F. Org. Lett. 2011, 13, 832
42. Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 6801
43. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656
44. Kouznetsov, V. V. Tetrahedron 2009, 65, 2721
45. Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099
46. Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357
47. Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973
48. Akiyama, T.; Morita, H.; Fuchibe, K. J. Am. Chem. Soc. 2006, 128, 13070
49. Liu, H.; Dagousset, G.; Masson, G.; Retailleau, P.; Zhu, J. J. Am. Chem. Soc. 2009, 131, 4598
50. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
51. Matsubara, R.; Kobayashi, S. Acc. Chem. Res. 2008, 41, 292
52. Carbery, D. R. Org. Bioorg. Chem. 2008, 6, 3455
53. Nugenta, T. C.; El-Shazlya, M. Adv. Synth. Catal. 2010, 352, 753
54. Gopalaiah, K. and Kagan, H. B. Chem. Rev. 2011, 111, 4599
55. Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem., Int. Ed. 2006, 45, 2254
56. Terada, K.; Machioka, K.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 10336
57. Terada, M.; Soga, K.; Momiyama, N. Angew. Chem., Int. Ed. 2008, 47, 4122
58. Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem., Int. Ed. 2009, 48, 2553
59. Guo, Q.-X; Peng, Y.-G.; Zhang, J.-W.; Song, L.; Feng, Z.; Gong, L.-Z. Org. Lett. 2009, 11, 4620
60. Dagousset, G.; Drouet, F.; Masson, G.; Zhu, J. Org. Lett. 2009, 11, 5546
61. Lu, M.; Lu, Y.; Zeng, X.; Li, X.; Zhong, G. Angew. Chem., Int. Ed. 2010, 49, 8588
62. Wang, C.; Han, Z.-Y.; Luo, H.-W.; Gong, L.-Z. Org. Lett. 2010, 12, 2266
63. Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, in press (DOI: 10.1021/ar2000343).
64. Bergonzini, G.; Gramigna, L.; Mazzanti, A.; Fochi, M.; Bernardi, L.; Ricci, A. Chem. Commun. 2010, 46, 327
65. Xie, M.-S.; Chen, X.-H.; Zhu, Y.; Gao, B.; Lin, L.-L.; Liu, X.-H.; Feng, X.-M. Angew. Chem., Int. Ed. 2010, 49, 3799
66. Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986
67. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
68. Yu, X.; Wang, W. Chem. Asian J. 2008, 3, 516
69. Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999
70. Akiyama, T. Chem. Rev. 2007, 107, 5744
71. Terada, M. Chem. Commun. 2008, 4097
72. Terada, M. Synthesis 2010, 1929
73. Terada, M. Bull. Chem. Soc. Jpn. 2010, 83, 101
74. Kampen, D.; Reisinger, C. M.; List, B. Top. Curr. Chem. 2010, 291, 395
75. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566
76. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356
77. 4: Funabashi, M.; Iwakawa, J.; Yoshimura Bull. Soc. Chim. Jpn. 1969, 42, 2885
78. Jia, Y.-X.; Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q. Angew. Chem., Int. Ed. 2007, 46, 5565
79. Baudequin, C.; Zamfir, A.; Tsogoeva, S. B. Chem. Commun. 2008, 4637
80. Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2008, 130, 14452
81. Kobayashi, S.; Gustafsson, T.; Shimizu, Y.; Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8, 4923
82. Seayad, J.; List, B. Catalytic Asymmetric Multicomponent Reactions. In Multicomponent Reaction; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005; p 227.
83. Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602
84. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
85. Guillena, G.; Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 2007, 18, 693
86. Gong, L.-Z.; Chen, X.-H.; Xu, X.-Y. Chem. Eur. J. 2007, 13, 8920
87. Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855
88. Katritzky, A.; Rachwak, B.; Rachwal, S. J. Org. Chem. 1995, 60, 3993
89. Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287
90. Ma, Y.; Qian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462
91. Crousse, B.; Bégué, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009
92. Talukdar, S.; Chen, C.-T.; Fang, J.-M. J. Org. Chem. 2000, 65, 3148
93. Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362
94. Yadav, J. S.; Subba Reddy, B. V.; Srinivas, R.; Madhuri, C.; Ramalingam, T. Synlett 2001, 240
95. Lavilla, R.; Bernadeu, M. C.; Carranco, I.; Díaz, J. L. Org. Lett. 2003, 5, 717
96. Powell, D. A.; Batey, R. A. Tetrahedron Lett. 2003, 44, 7569
97. Legros, J.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D. Synlett 2006, 1899
98. Hadden, M.; Nieuwenhuyzen, M.; Osborne, D.; Stevenson, P. J.; Thompson, N.; Walker, A. D. Tetrahedron 2006, 62, 3977
99. Xu, S.; Wang, Z.; Zhang, X.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2008, 47, 2840
100. Hatano, M.; Moriyama, K.; Maki, T.; Ishihara, K. Angew. Chem., Int. Ed. 2010, 49, 3823
101. Klussmann, M.; Ratjen, L.; Hoffmann, S.; Wakchaure, V.; Goddard, R.; List, B. Synlett 2010, 2189
102. Rueping, M.; Theissmann, T.; Kuenkel, A.; Koenigs, R. M. Angew. Chem., Int. Ed. 2008, 47, 6798
103. Rueping, M.; Nachtsheim, B. J.; Koenigs, R. M.; Ieawsuwan, W. Chem. Eur. J. 2010, 16, 13116
104. Hatano, M.; Ikeno, T.; Matsumura, T.; Torii, S.; Ishihara, K. Adv. Synth. Catal. 2008, 350, 1776
105. Yue, T.; Wang, M.-X.; Wang, D.-X.; Masson, G.; Zhu, J. J. Org. Chem. 2009, 74, 8396
106. Lv, J.; Li, X.; Zhong, L.; Luo, S.; Cheng, P. Org. Lett. 2010, 12, 1096
107. Rueping, M.; Nachtsheim, B. J.; Koenigs, R. M.; Ieawsuwan, W. Chem. Eur. J. 2010, 16, 13116
108. Ingle, G. K.; Liang, Y.; Mormino, M. G.; Li, G.; Fronczek, F. R.; Antilla, J. C. Org. Lett. 2011, 13, 2054
109. Zheng, W.; Zhang, Z.; Kaplan, M. J.; Antilla, J. C. J. Am. Chem. Soc. 2011, 133, 3339
110. Larson, S. E.; Li, G.; Rowland, G. B.; Junge, D.; Huang, R.; Woodcock, H. L.; Antilla, J. C. Org. Lett. 2011, 13, 2188
111. Zhang, Z.; Zheng, W.; Antilla, J. C. Angew. Chem., Int. Ed. 2011, 50, 1135
112. Drouet, F.; Lalli, C.; Liu, H.; Masson, G.; Zhu, J. Org. Lett. 2011, 13, 94
113. Rueping, M.; Bootwicha, T.; Sugiono, E. Synlett 2011, 323
114. Terada, M.; Kanomata, K. Synlett 2011, 1255
115. Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2999
116. Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem. Eur. J. 2010, 16, 9350
117. Harder, S. Chem. Rev. 2010, 110, 3852
118. Kobayashi, S.; Ishitani, H.; Nakagawa, S. Synthesis 1995, 1195
119. Hermitage, S.; Jayb, D. A.; Whiting, A. Tetrahedron Lett. 2002, 43, 9633
120. Stevenson, P. J.; Graham, I. Arkivoc 2003, 139
121. Carranco, I.; Díaz, J. L.; Jiménez, O.; Lavilla, R. Tetrahedron Lett. 2003, 44, 8449
122. Sridharan, V.; Avendaño, C.; Menéndez, J. C. Synthesis 2008, 1039
123. Alves, M. J.; Azoia, N. G.; Fortes, A. G. Tetrahedron 2007, 63, 727
124. Shindoh, N.; Tokuyama, H.; Takemoto, Y.; Takasu, K. J. Org. Chem. 2008, 73, 7451
125. Beifuss, U.; Ledderhose, S.; Ondrus, V. Arkivoc 2005, 147
126. Stevenson, P. J.; Nieuwenhuyzen, M.; Osborne, D. Arkivoc 2007, 12
127. McCarrick, M. A.; Wu, Y.-D.; Houk, K. N. J. Org. Chem. 1993, 58, 3330
128. Whiting, A.; Windsor, C. M. Tetrahedron 1998, 54, 6035
129. Bello, D.; Ramón, Lavilla, R. Curr. Org. Chem. 2010, 14, 332
130. Jiménez, O.; de la Rosa, G.; Lavilla, R. Angew. Chem., Int. Ed. 2005, 44, 6521
131. Isambert, N; Cruz, M.; Arévalo, M. J.; Gómez, E.; Lavilla, R. Org. Lett. 2007, 9, 4199
132. Bernardi, L.; Comes-Franchini, M.; Fochi, M.; Leo, V.; Mazzanti, A.; Ricci, A. Adv. Synth. Catal. 2010, 352, 3399
133. Tertiary enamides as nucleophiles: Yang, L.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. J. Am. Chem. Soc. 2009, 131, 10390
134. Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520
135. Pregosin, P. S. Pure Appl. Chem. 2009, 81, 615
136. Mechanistic studies by mass spectroscopy: Schrader, W.; Handayani, P. P.; Zhou, J.; List, B. Angew. Chem., Int. Ed. 2009, 48, 1463
137. Sharma, G. M.; Roels, O. A. J. Org. Chem. 1973, 38, 3648
138. Bissonnetteh, M.; Le Thanh, H.; Vocelle, D. Can. J. Chem. 1985, 63, 2298
139. Knorr, R.; Ferchland, K. Liebigs Ann. 1995, 419
140. Yue, T.; Wang, M.-X.; Wang, D.-X.; Masson, G.; Zhu, J. Angew. Chem., Int. Ed. 2009, 48, 6717
141. Fleischmann, M., Drettwan, D., Sugiono, E., Rueping, M., and Gschwind, R. M. Angew. Chem., Int. Ed. 2011, 50, 6364
142. Li, N.; Chen, X.-H.; Zhou, S.-M.; Luo, S.-W.; Song, J.; Ren, L.; Gong, L.-Z. Angew. Chem., Int. Ed. 2010, 49, 6378
143. Satyanarayana, T.; Abrahm, S.; Kagan, H. B. Angew. Chem., Int. Ed. 2009, 48, 456
144. Simón, L.; Goodman, J. M. J. Org. Chem. 2011, 76, 1775
145. Cheong, P. H.-Y.; Legault, C. Y.; Um, J. M.; Çelebi- Ölcüm, N.; Houk, K. N. Chem. Rev. 2011, 111, 5042