Enantioselective Michael/Mannich polycyclization cascade of indolyl enones catalyzed by quinine-derived primary amines

Angewandte Chemie - International Edition

Volumn 50, Issue 37, 2011, Pages 8665-8669

  Cai, Quan ^a   Zheng, Chao ^a   Zhang, Jun Wei ^a   You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

amines; asymmetric catalysis; cascade reactions; indoles; organocatalysis

Indexed keywords

ASYMMETRIC CATALYSIS; CASCADE REACTIONS; CHIRAL CENTERS; DIASTEREO-SELECTIVITY; ENANTIOSELECTIVE; INDOLES; ORGANOCATALYSIS; POLYCYCLIZATION; PRIMARY AMINES;

CATALYSIS; ENANTIOSELECTIVITY; REACTION KINETICS;

AMINES;

AMINE; KETONE; QUININE;

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

AMINES; CATALYSIS; CYCLIZATION; KETONES; MOLECULAR STRUCTURE; QUININE; STEREOISOMERISM;

EID: 80052498685     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103937     Document Type: Article

References (128)

1. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
2. Angew. Chem. Int. Ed. 2006, 45, 7134
3. C. J. Chapman, C. G. Frost, Synthesis 2007, 1
4. A. M. Walji, D. W. C. MacMillan, Synlett 2007, 1477
5. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232
6. Angew. Chem. Int. Ed. 2008, 47, 6138
7. A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922
8. H. M. L. Davies, E. J. Sorensen, Chem. Soc. Rev. 2009, 38, 2981
9. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993
10. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167, and references therein.
11. N. Kagawa, J. P. Malerich, V. H. Rawal, Org. Lett. 2008, 10, 2381, and references therein
12. K. Eastman, P. S. Baran, Tetrahedron 2009, 65, 3149
13. Q.-F. Wu, H. He, W.-B. Liu, S.-L. You, J. Am. Chem. Soc. 2010, 132, 11418.
14. R. B. Woodward, M. P. Cava, W. D. Ollis, A. Hunger, H. U. Daeniker, K. Schenker, J. Am. Chem. Soc. 1954, 76, 4749
15. R. B. Woodward, M. P. Cava, W. D. Ollis, A. Hunger, H. U. Daeniker, K. Schenker, Tetrahedron 1963, 19, 247
16. S. P. Marsden, K. M. Depew, S. J. Danishefsky, J. Am. Chem. Soc. 1994, 116, 11143
17. F. He, Y. Bo, J. D. Altom, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 6771
18. S. Lucarini, F. Bartoccini, F. Battistoni, G. Diamantini, G. Piersanti, M. Righi, G. Spadoni, Org. Lett. 2010, 12, 3844
19. T. Newhouse, C. A. Lewis, K. J. Eastman, P. S. Baran, J. Am. Chem. Soc. 2010, 132, 7119
20. Z.-W. Zuo, W.-Q. Xie, D.-W. Ma, J. Am. Chem. Soc. 2010, 132, 13226
21. H.-X. Wu, F. Xue, X. Xiao, Y. Qin, J. Am. Chem. Soc. 2010, 132, 14052.
22. J. F. Austin, S.-G. Kim, C. J. Sinz, W.-J. Xiao, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2004, 101, 5482
23. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314
24. S. B. Jones, B. Simmons, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 13606
25. L. M. Repka, J. Ni, S. E. Reisman, J. Am. Chem. Soc. 2010, 132, 14418
26. C.-W. Zheng, Y.-P. Lu, J.-K. Zhang, X.-K. Chen, Z. Chai, W.-Y. Ma, G. Zhao, Chem. Eur. J. 2010, 16, 5853
27. R. R. Knowles, J. Carpenter, S. B. Blakey, A. Kayano, I. K. Mangion, C. J. Sinz, D. W. C. MacMillan, Chem. Sci. 2011, 2, 308; for a recent racemic example, see
28. G. Cera, P. Crispino, M. Monari, M. Bandini, Chem. Commun. 2011, DOI:.
29. T. M. Kutchan, The Alkaloids: Chemistry and Biology, Vol. 50 (Ed.:, G. A. Cordell,), Academic Press, London, 1998, pp. 257-316
30. P. R. Blakemore, J. D. White, Chem. Commun. 2002, 1159
31. G. Dondio, S. Ronzoni, D. S. Eggleston, M. Artico, P. Petrillo, G. Petrone, L. Visentin, C. Farina, V. Vecchietti, G. D. Clarke, J. Med. Chem. 1997, 40, 3192
32. R. Sakai, T. Higa, C. W. Jefford, G. Bernardinelli, J. Am. Chem. Soc. 1986, 108, 6404
33. J. Kobayashi, M. Tsuda, M. Ishibashi, Pure Appl. Chem. 1999, 71, 1123
34. J. D. Winkler, J. M. Axten, J. Am. Chem. Soc. 1998, 120, 6425
35. S. F. Martin, J. M. Humphrey, A. Ali, M. C. Hillier, J. Am. Chem. Soc. 1999, 121, 866.
36. Q. Cai, Z.-A. Zhao, S.-L. You, Angew. Chem. 2009, 121, 7564
37. Angew. Chem. Int. Ed. 2009, 48, 7428
38. Q. Cai, C. Zheng, S.-L. You, Angew. Chem. 2010, 122, 8848
39. Angew. Chem. Int. Ed. 2010, 49, 8666.
40. L. Turet, I. E. Markõ, B. Tinant, J.-P. Declercq, R. Touillaux, Tetrahedron Lett. 2002, 43, 6591
41. N. Heureux, J. Wouters, I. E. Markõ, Org. Lett. 2005, 7, 5254
42. N. Heureux, J. Wouters, B. Norberg, I. E. Markõ, Org. Biomol. Chem. 2006, 4, 3898.
43. A chiral primary amine salt was first applied as an iminium catalyst by Ishihara and co-workers
44. K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2005, 127, 10504
45. A. Sakakura, K. Suzuki, K. Nakano, K. Ishihara, Org. Lett. 2006, 8, 2229
46. A. Sakakura, K. Suzuki, K. Ishihara, Adv. Synth. Catal. 2006, 348, 2457
47. K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2007, 129, 8930
48. K. Ishihara, A. Sakakura, M. Hatano, Synlett 2007, 686
49. K. Ishihara, K. Nakano, M. Akakura, Org. Lett. 2008, 10, 2893; For reviews on chiral primary amine catalysis, see
50. G. Bartoli, P. Melchiorre, Synlett 2008, 1759
51. Y.-C. Chen, Synlett 2008, 1919
52. F. Peng, Z. Shao, J. Mol. Catal. A 2008, 285, 1
53. L.-W. Xu, Y. Lu, Org. Biomol. Chem. 2008, 6, 2047
54. L.-W. Xu, J. Luo, Y. Lu, Chem. Commun. 2009, 1807.
55. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79
56. A. Erkkila, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416.
57. D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1567
58. Angew. Chem. Int. Ed. 2007, 46, 1545
59. X. Yu, W. Wang, Org. Biomol. Chem. 2008, 6, 2037; for selected examples, see
60. T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951
61. J. W. Yang, M. T. Hechavarria Fonseca, B. List, J. Am. Chem. Soc. 2005, 127, 15036
62. Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051
63. M. Marigo, T. Schulte, J. Franzén, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15710
64. W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354
65. B. Simmons, A. M. Walji, D. W. C. MacMillan, Angew. Chem. 2009, 121, 4413
66. Angew. Chem. Int. Ed. 2009, 48, 4349
67. X. Zhang, S. Zhang, W. Wang, Angew. Chem. 2010, 122, 1523
68. Angew. Chem. Int. Ed. 2010, 49, 1481.
69. J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393
70. Angew. Chem. Int. Ed. 2007, 46, 389
71. J.-W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J.-G. Deng, Y.-C. Chen, Org. Lett. 2007, 9, 413
72. W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2007, 5, 816
73. G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403
74. W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007, 119, 7811
75. Angew. Chem. Int. Ed. 2007, 46, 7667
76. A. Carlone, G. Bartoli, M. Bosco, F. Pesciaioli, P. Ricci, L. Sambri, P. Melchiorre, Eur. J. Org. Chem. 2007, 5492
77. P. Ricci, A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Adv. Synth. Catal. 2008, 350, 49
78. P. Ricci, A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Org. Biomol. Chem. 2008, 6, 349
79. R. P. Singh, K. Bartelson, Y. Wang, H. Su, X. Lu, L. Deng, J. Am. Chem. Soc. 2008, 130, 2422
80. X. Lu, L. Deng, Angew. Chem. 2008, 120, 7824
81. Angew. Chem. Int. Ed. 2008, 47, 7710
82. S. Gogoi, C.-G. Zhao, D. Ding, Org. Lett. 2009, 11, 2249
83. M. W. Paixão, N. Holub, C. Vila, M. Nielsen, K. A. Jørgensen, Angew. Chem. 2009, 121, 7474
84. Angew. Chem. Int. Ed. 2009, 48, 7338
85. E. Zhang, C.-A. Fan, Y.-Q. Tu, F.-M. Zhang, Y.-L. Song, J. Am. Chem. Soc. 2009, 131, 14626
86. C. Liu, Y. Lu, Org. Lett. 2010, 12, 2278
87. J. Lv, H. Wu, Y. Wang, Eur. J. Org. Chem. 2010, 2073
88. N. Holub, H. Jiang, M. W. Paixão, C. Tiberi, K. A. Jørgensen, Chem. Eur. J. 2010, 16, 4337
89. Z. Qiao, Z. Shafiq, L. Liu, Z.-B. Yu, Q. Zheng, D. Wang, Y.-J. Chen, Angew. Chem. 2010, 122, 7452
90. Angew. Chem. Int. Ed. 2010, 49, 7294
91. X.-M. Li, B. Wang, J.-M. Zhang, M. Yan, Org. Lett. 2011, 13, 374
92. J.-B. Ling, W.-P. Wang, P.-F. Xu, ChemCatChem 2011, 3, 302; for selected enamine catalysis by cinchona-alkaloid-derived primary amines, see
93. S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599
94. T.-Y. Liu, H.-L. Cui, Y. Zhang, K. Jiang, W. Du, Z.-Q. He, Y.-C. Chen, Org. Lett. 2007, 9, 3671
95. J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. 2008, 120, 7677
96. Angew. Chem. Int. Ed. 2008, 47, 7565
97. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem. 2010, 122, 9879
98. Angew. Chem. Int. Ed. 2010, 49, 9685
99. P. Kwiatkowski, T. D. Beeson, J. C. Conrad, D. W. C. MacMillan, J. Am. Chem. Soc. 2011, 133, 1738
100. A. Lee, A. Michrowska, S. Sulzer-Mosse, B. List, Angew. Chem. 2011, 123, 1745
101. Angew. Chem. Int. Ed. 2011, 50, 1707
102. C. Liu, Q. Zhu, K.-W. Huang, Y. Lu, Org. Lett. 2011, 13, 2638; for selected iminium-enamine cascade catalysis by cinchona alkaloid derived primary amine, see
103. X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070
104. C. M. Reisinger, X. Wang, B. List, Angew. Chem. 2008, 120, 8232
105. Angew. Chem. Int. Ed. 2008, 47, 8112
106. F. Pesciaioli, F. De Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. 2008, 120, 8831
107. Angew. Chem. Int. Ed. 2008, 47, 8703
108. X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc. 2008, 130, 8134
109. J. Lv, J. Zhang, Z. Lin, Y. Wang, Chem. Eur. J. 2009, 15, 972
110. P. Galzerano, F. Pesciaioli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 8032
111. Angew. Chem. Int. Ed. 2009, 48, 7892
112. O. Lifchits, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2010, 132, 10227
113. X. Sun, F. Yu, T. Ye, X. Liang, J. Ye, Chem. Eur. J. 2011, 17, 430
114. B. Tan, N. R. Candeias, C. F. Barbas III, Nat. Chem. 2011, 3, 473; for selected enamine/iminium cascade catalysis by cinchona alkaloid derived primary amine, see
115. L.-Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7332
116. Angew. Chem. Int. Ed. 2009, 48, 7196
117. C. Cassani, X. Tian, E. C. Escudero-Adán, P. Melchiorre, Chem. Commun. 2011, 47, 233
118. G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M.-P. Song, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7336
119. Angew. Chem. Int. Ed. 2009, 48, 7200; for selected Lewis base catalysis by cinchona-alkaloid-derived primary amines, see
120. B. Tan, P. J. Chua, Y. Li, G. Zhong, Org. Lett. 2008, 10, 2437
121. B. Tan, Z. Shi, P. J. Chua, G. Zhong, Org. Lett. 2008, 10, 3425
122. B. Tan, P. J. Chua, X. Zeng, M. Lu, G. Zhong, Org. Lett. 2008, 10, 3489.
123. The absolute configuration was determined by the X-ray diffraction analysis of enantiopure 3 b. CCDC 808361 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
124. Since only two diastereoisomers were isolated, the origin of the diastereoselectivity was studied by computational method. The DFT calculations suggested that the Mannich reaction is stereospecific because of the rigid polycylic skeleton. The cis-fused [4.3.0] bicyclic structure is the only accessible product of the cyclization process. See the Supporting Information for details.
125. The relative configurations of 3 k and 3 k' were determined by the X-ray diffraction. CCDC 828201 and 828107 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
126. J. Fridrichsons, A. Mcl. Mathieson, M. F. Mackay, Tetrahedron 1970, 26, 1869
127. T. Kametani, T. Kohno, R. Charubala, K. Fukumoto, Tetrahedron 1972, 28, 3227.
128. J. Sapi, S. Dridi, J. Laronze, F. Sigaut, D. Patigny, J.-Y. Laronze, J. Lévy, Tetrahedron 1996, 52, 8209.