An efficient enantioselective method for asymmetric friedel-crafts alkylation of indoles with α,β-unsaturated aldehydes

Advanced Synthesis and Catalysis

Volumn 351, Issue 5, 2009, Pages 772-778

  Hong, Liang ^a   Wang, Lei ^a   Chen, Chao ^b   Zhang, Bangzhi ^a   Wang, Rui ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

, unsaturated aldehydes; Friedel crafts reaction; Indoles; Michael addition; Organic catalysis

Indexed keywords

EID: 63349093955     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800710     Document Type: Article

References (97)

1. G. A. Olah, R. Krishnamurti, G. K. S. Prakash, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, Vol. 3, pp 293-339.
2. For selected reviews of organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
3. Angew. Chem. Int. Ed. 2004, 43, 5138;
4. b) special issue on organocatalysis: Ace. Chem. Res. 2004, 37, issue 8;
5. c) J. Seayad, B. List, Org. Biomol. Chem. 2005, 5, 719;
6. d) B. List, J. W. Yang, Science 2006, 313, 1584;
7. e) B. List, Chem. Commun. 2006, 819;
8. f) M. J. Gaunt, C. C. Johansson, A. McNally, N. T. Vo, Drug Discovery Today, 2007, 72, 8;
9. g) special issue on organocatalysis: Chem. Rev. 2007, 107, issue 12;
10. h) P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim (Germany), 2007;
11. i) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
12. Angew. Chem. Int. Ed. 2008, 47, 4638.
13. For recent reviews of Friedel-Crafts alkylation reaction, see: a) M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560;
14. Angew. Chem. Int. Ed. 2004, 43, 550;
15. b) K. A. Jørgensen, Synthesis 2003, 1117;
16. c) S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873;
17. d) Y. Wang, K-L. Ding, Chin. J. Org. Chem. 2001, 27, 763;
18. e) T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903.
19. J. H. Clark, (Ed.), Chemistry of Waste Minimisation, Chapman and Hall, London, 1995.
20. For examples of potential medicinal agents, see: a) S. E. Draheim, N. J. Bach, R. D. Dillard, D. R. Berry, D. G. Carlson, N. Y. Chirgadze, D. K. Clawson, L. W. Hartley, L. M. Johnson, N. D. Jones, E. R. McKinney, E. D. Mihelich, J. L. Olkowski, R. W. Schevitz, A. C. Smith, D. W. Snyder, C. D. Sommers, J. P. Wery, J. Med. Chem. 1996, 39, 5159;
21. b) D. J. Rawson, K. N. Dack, R. P. Dickinson, K. James, Bioorg. Med. Chem. Lett. 2002, 12, 125;
22. c) J. Chang-Fong, J. B. Rangisetty, M. Dukat, V. Setola, T. Raffay, B. Roth, R. A. Glennon, Bioorg. Med. Chem. Lett. 2004, 14, 1961;
23. d) A. C. Kinsman, M. A. Kerr, J. Am. Chem. Soc. 2003, 125, 14120.
24. For selected examples of Friedel-Crafts alkylation of indoles with bidentate chelating carbonyl substrates, see: a) K. B. Jensen, J. Thorhauge, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2001, 113, 164;
25. Angew. Chem. Int. Ed. 2001, 40, 160;
26. b) M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603;
27. Angew. Chem. Int. Ed. 2008, 47, 593;
28. c) D. A. Evans, K. A. Scheidt, K. R. Fandrick, H. W. Lam, J. Wu, J. Am. Chem. Soc. 2003, 125, 10780;
29. d) J. Zhou, Y. Ting, J. Am. Chem. Soc. 2002, 124, 9030;
30. e) J. Zhou, Y. Tang. Chem. Commun. 2004, 432;
31. f) W. Zhuang, T. Hansen, K. A. Jørgensen, Chem. Commun. 2001, 347;
32. g) C. Palomo, M. Oiarbide, B. G. Kardak, J. M. García, A. Linden, J. Am. Chem. Soc. 2005, 127, 4154;
33. h) D. A. Evans, K. R. Fandrick, H. J. Song, J. Am. Chem. Soc. 2005, 127, 8942;
34. i) Y. X. Jia, S. F. Zhu, Y. Yang, Q. L. Zhou, J. Org. Chem. 2006, 71, 75;
35. j) W. Zhuang, R. G. Hazell, K. A. Jørgensen, Org. Biomol. Chem. 2005, 5, 2566;
36. k) R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 6734;
37. Angew. Chem. Int. Ed. 2005, 44, 6576;
38. l) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2008, 120, 4080;
39. Angew. Chem. Int. Ed. 2008, 47, 4016;
40. m) Q. Kang, Z. A. Zhao, S. L. You, J. Am. Chem. Soc. 2007, 129, 1484.
41. For selected examples of Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones by metal catalysis, see: a) M. Bandini, M. Fagioli, M. Garavelli, A. Melloni, V. Trigari, A. Umani-Ronchi, J. Org. Chem. 2004, 69, 7511;
42. b) M. Bandini, M. Fagioli, P. Melchiorre, A. Melloni, A. Umani-Ronchi, Tetrahedron Lett. 2003, 44, 5843;
43. c) G. Blay, I. Fernández, J. R. Pedro, C. Vila, Org. Lett. 2007, 9, 2601.
44. For selected examples of Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones by organocatalysis, see: a) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403;
45. b) D.-P. Li, Y.-C. Guo, Y. Ding, W-J. Xiao, Chem. Commun. 2006, 799;
46. c) W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-G Chen, Org. Biomol. Chem. 2007, 5, 816;
47. d) W. Zhou, L.-W. Xu, L. Li, L. Yang, C.-G. Xia, Eur. J. Org. Chem. 2006, 5225;
48. e) H.-Y. Tang, A.-D. Lu, Z.-H. Zhou, G.-F. Zhao, L.-N. He, C. C. Tang, Eur. J. Org. Chem. 2008, 1406.
49. For selected examples of α,β-unsaturated aldehydes as electrophiles in Friedel-Crafts alkylation, see: a) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370;
50. b) J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172;
51. c) N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 7894;
52. d) J. F. Austin, S. G. Kim, C. J. Sinz, W.-J. Xiao, D. W. C. MacMillan, Proc. Natl. Acad. Sci USA 2004, 101, 5482;
53. e) H. D. King, Z. Meng, D. Denhart, R. Mattson, R. Kimura, D. Wu, Q. Gao, J. E. Macor, Org. Lett. 2005, 7, 3437;
54. f) C. F. Li, H. Liu, J. Liao, Y. J. Cao, X. P. Liu, W. J. Xiao, Org. Lett. 2007, 9, 1847.
55. For recent reviews of iminium catalysis, see: a) A. Erkkilä, I. Maj ander, P. M. Pihko, Chem. Rev. 2007, 107, 5416;
56. b) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701.
57. For selected examples of tertiary amine to activate indole, see: a) B. Török, M. Abid, G. London, J. Esquibel, M. Török, S. C. Mhadgut, P. Yan, G. K. S. Prakash, Angew. Chem. 2005, 117, 3146;
58. Angew. Chem. Int. Ed. 2005, 44, 3086;
59. b) H. Li, Y. Q. Wang, L. Deng, Org. Lett. 2006, 8, 4063;
60. c) Y. Q. Wang, J. Song, R. Hong, H. Li, L. Deng, J. Am. Chem. Soc. 2006, 128, 8156.
61. For recent examples using diarylprolinol ethers as an organocatalyst, see: a) M. Marigo, T. Schulte, J. Franzén, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15710;
62. b) S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411;
63. Angew. Chem. Int. Ed. 2006, 45, 4305;
64. c) M. Marigo, S. Bertelsen, A. Landa, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 5475;
65. d) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
66. Angew. Chem. Int. Ed. 2005, 44, 4212;
67. e) H. Gotoh, R. Masui, H. Ogino, M. Shoji, Y. Hayashi, Angew. Chem. 2006, 118, 7007;
68. Angew. Chem. Int. Ed. 2006, 45, 6853;
69. f) Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010;
70. Angew. Chem. Int. Ed. 2007, 46, 4922;
71. g) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354;
72. h) I. Ibrahem, R. Rios, J. Vesely, P. Hammar, L. Eriksson, F. Himo, A. Córdova, Angew. Chem. 2007, 119, 4591;
73. Angew. Chem. Int. Ed. 2007, 46, 4507;
74. i) S. Zhu, S. Yu, D. Ma, Angew. Chem. 2008, 120, 555;
75. Angew. Chem. Int. Ed. 2008, 47, 545;
76. j) H. Li, L. Zu, H. Xie, J. Wang, W. Jiang, W. Wang, Org. Lett. 2007, 9, 1833;
77. k) J. Vesely, I. Ibrahem, R. Rios, G.-L. Zhao, Y. Xu, A. Córdova, Tetrahedron Lett. 2007, 48, 2193;
78. l) A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588;
79. Angew. Chem. Int. Ed. 2007, 46, 4504;
80. m) Y. Chi, S. H. Gellman, J. Am. Chem. Soc. 2006, 128, 6804;
81. n) Y. Wang, P. Li, X. Liang, J. Ye, Adv. Synth. Catal. 2008, 350, 1383;
82. o) for a review see: C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042;
83. Angew. Chem. Int. Ed. 2006, 45, 7876.
84. [9b]
85. For selected examples of Brønsted acids accelerating amine-catalyzed reactions, see: a) N. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 2527;
86. b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260;
87. c) M. Nakadai, S. Saito, H. Yamamoto, Tetrahedron 2002, 58, 8167;
88. d) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. 2004, 116, 2474;
89. Angew. Chem. Int. Ed. 2004, 43, 2420;
90. e) Y. Xu, A. Córdova, Chem. Commun. 2006, 460;
91. f) P. Dinér, M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 2029;
92. Angew. Chem. Int. Ed. 2007, 46, 1983.
93. An example with triethylamine as an acid scavenger, see: R. Rios, H. Sundén, J. Vesely, G.-L. Zhao, P. Dziedzic, A. Córdova, Adv. Synth. Catal. 2007, 349, 1028.
94. For selected examples on using NaOAc as a base additive in iminium-based conjugate addition, see: a) H. Li, J. Wang, H. Xie, L. Zu, W. Jiang, E. N. Duesler, W. Wang, Org. Lett. 2007, 9, 965;
95. b) J. Wang, H. Li, H. Xie, L. Zu, X. Shen, W. Wang, Angew. Chem. 2007, 119, 9208;
96. Angew. Chem. Int. Ed. 2007, 46, 9050.
97. D. J. Bailey, D. O'Hagan, M. Tavasli, Tetrahedron: Asymmetry 1997, 8, 149.