Asymmetrie construction of polycyclic indoles through olefin cross-metathesis/intramolecular friedel-crafts alkylation under sequential catalysis

Angewandte Chemie - International Edition

Volumn 48, Issue 40, 2009, Pages 7428-7431

  Cai, Quan ^a   Zhao, Zhuo An ^a   You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric catalysis; Chiral br nsted acids; Friedel crafts alkylation; Indoles; Sequential catalysis

Indexed keywords

ASYMMETRIC CATALYSIS; CASCADE REACTIONS; FRIEDEL-CRAFTS ALKYLATION; INDOLES; SEQUENTIAL CATALYSIS; STARTING MATERIALS;

ACIDS; ALKYLATION; ENANTIOSELECTIVITY; OLEFINS;

CATALYSIS;

EID: 70349931072     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903462     Document Type: Article

References (71)

1. For a review, see: a) Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745;
2. for recent examples, see: b) V. Komanduri, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 16448;
3. c) S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336;
4. d) M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027;
5. Angew. Chem. Int. Ed. 2007, 46, 6903;
6. e) W-H. Hu, X.-F. Xu, J. Zhou, W.-J. Liu, H.-X. Huang, J. Hu, L.-P. Yang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 7782;
7. f) C. Q. Li, C. Wang, B. Villa-Marcos, J. L. Xiao, J. Am. Chem. Soc. 2008, 130, 14450;
8. g) K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2008, 130, 14452;
9. h) B. M. Trost, N. Maulide, R. C. Livingston, J. Am. Chem. Soc. 2008, 130, 16502;
10. i) M. Terada, Y. Toda, J. Am. Chem. Soc. 2009, 131, 6354;
11. j) C. Li, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2009, 131, 6967;
12. k) B. Simmons, A. M. Walji, D. W. C. MacMillan, Angew. Chem. 2009, 121, 4413;
13. Angew. Chem. Int. Ed. 2009, 48, 4349;
14. l) Z.-Y. Han, H. Xiao, X.-H. Chen, L.-Z. Gong, J. Am. Chem. Soc. 2009, 131, 9182.
15. For reviews, see: a) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292;
16. Angew. Chem. Int. Ed. 2006, 45, 7134;
17. b) C. J. Chapman, C. G. Frost, Synthesis 2007, 1;
18. c) A. M. Walji, D. W. C. MacMillan, Synlett 2007, 1477;
19. d) D. Enders, C. Grondai, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590;
20. Angew. Chem. Int. Ed. 2007, 46, 1570;
21. e) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232;
22. Angew. Chem. Int. Ed. 2008, 47, 6138;
23. f) A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922;
24. g) Y. J. Park, J. W Park, C. H. Jun, Acc. Chem. Res. 2008, 41, 222.
25. For reviews on catalysis by chiral phosphoric acids, see: a) M. S. Taylor, E. N Jacobsen, Angew. Chem. 2006, 118, 1550;
26. Angew. Chem. Int. Ed. 2006, 45, 1520;
27. b) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999;
28. c) S. J. Connon, Angew. Chem. 2006, 118, 4013;
29. Angew. Chem. Int. Ed. 2006, 45, 3909;
30. d) T. Akiyama, Chem. Rev. 2007, 107, 5744;
31. e) X. Yu, W. Wang, Chem. Asian J. 2008, 3, 516;
32. f) M. Terada, Chem. Commun. 2008, 4097;
33. g) G. Adair, S. Mukherjee, B. List, Aldrichimica Acta 2008, 41, 31.
34. For reviews on asymmetric Friedel-Crafts reactions, see: a) M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560;
35. Angew. Chem. Int. Ed. 2004, 43, 550;
36. b) M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett 2005, 1199;
37. c) T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903;
38. d) S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190.
39. For selected examples, see: a) H. Yamada, T. Kawate, M. Matsumizu, A. Nishida, K. Yamaguchi, M. Nakagawa, J. Org. Chem. 1998, 63, 6348;
40. b) M. Agnusdei, M. Bandini, A. Melloni, A. Umani-Ronchi, J. Org. Chem. 2003, 68, 7126;
41. c) M. Bandini, A. Melloni, F. Piccinelli, R. Sinisi, S. Tommasi, A. Umani-Ronchi, J. Am. Chem. Soc. 2006, 128, 1424;
42. d) X.-Q. Han, R. A. Widenhoefer, Org. Lett. 2006, 8, 3801;
43. e) H. Huang, P. René, Angew. Chem. 2009, 121, 612;
44. Angew. Chem. Int. Ed. 2009, 48, 604.
45. For organocatalyzed asymmetric Pictet-Spengler reactions, see: a) M. S. Taylor, E. N Jacobsen, J. Am. Chem. Soc. 2004, 126, 10558;
46. b) J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086;
47. c) M. J. Wanner, R. N. S. van der Haas, K. R. de Cuba, J. H. van Maarseveen, H. Hiemstra, Angew. Chem. 2007, 119, 7629;
48. Angew. Chem. Int. Ed. 2007, 46, 7485;
49. d) J. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404;
50. e) D J. Mergott, S. J. Zuend, E. N. Jacobsen, Org. Lett. 2008, 10, 745;
51. f) J. T. Raheem, P. S. Thiara, E. N. Jacobsen, Org. Lett. 2008, 10, 1577;
52. g) N. V. Sewgobind, M. J. Wanner, S. Ingemann, R. von Gelder, J. H. van Maarseveen, H. Hiemstra, J. Org. Chem. 2008, 73, 6405.
53. a) E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797;
54. b) E. L. Larghi, T. S. Kaufman, Synthesis 2006, 187.
55. For successful examples, see: a) D A. Evans, K. R. Fandrick, H.J. Song, J. Am. Chem. Soc. 2005, 127, 8942;
56. b) M. Angeli, M. Bandini, A. Garelli, F. Piccinelli, S. Tommasi, A. Umani-Ronchi, Org. Biomol. Chem. 2006, 4, 3291;
57. c) C.-F. Li, H. Liu, J. Liao, Y.J. Cao, X.-P. Liu, W.-P. Xiao, Org. Lett. 2007, 9, 1847;
58. d) H.-H. Lu, H. Liu, W Wu, X.-F. Wang, L.-Q. Lu, W-J. Xiao, Chem. Eur. J. 2009, 15, 2742.
59. J.-R. Chen, C.-F. Li, X.-L. An, J.-J. Zhang, X.-Y. Zhu, W.-J. Xiao, Angew. Chem. 2008, 120, 2523;
60. Angew. Chem. Int. Ed. 2008, 47, 2489.
61. a) Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484;
62. b) M. Zeng, Q. Kang, Q.-L. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 2169;
63. c) Q. Kang, X.-J. Zheng, S.-L. You, Chem. Eur. J. 2008, 14, 3539;
64. d) Q. Kang, Z.-A. Zhao, S.-L. You, Tetrahedron 2009, 65, 1603;
65. e) Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, S.-L. You, Chem. Eur. J. 2009, 15, 3351;
66. f) F.-L. Sun, M. Zeng, Q. Gu, S.-L. You, Chem. Eur. J. 2009, DOI: 10.1002/ chem.200901369.
67. For intermolecular Friedel-Crafts reactions of indoles with α,βunsaturated ketones, see: a) M. Bandini, M. Fagioli, M. Garavelli, A. Melloni, V. Trigari, A. Umani-Ronchi, J. Org. Chem. 2004, 69, 7511;
68. b) G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403;
69. c) H.-Y. Tang, A.-D. Lu, Z.-H. Zhou, G.-F. Zhao, L.-N. He, C.-C. Tang, Eur. J. Org. Chem. 2008, 1406.
70. CCDC736514 ((R)-2d) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
71. See the Supporting Information for details.