Highly enantioselective Friedel-Crafts alkylation of indole and pyrrole with β,γ-unsaturated α-ketoester catalyzed by chiral dicationic palladium complex

Tetrahedron Letters

Volumn 52, Issue 50, 2011, Pages 6682-6686

  Aikawa, Kohsuke ^a   Honda, Kazuya ^a   Mimura, Shunsuke ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Ene reaction; Friedel Crafts alkylation; Indole; Lewis acid; Pyrrole

Indexed keywords

ELECTROPHILE; ESTER; INDOLE; PALLADIUM COMPLEX; PYRROLE;

ARTICLE; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION;

EID: 80755135498     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.006     Document Type: Article

References (74)

1. C. Friedel, and J.M. Crafts C. R. Hebd. Seances Acad. Sci. 84 1877 1392
2. C. Friedel, and J.M. Crafts C. R. Hebd. Seances Acad. Sci. 84 1877 1450
3. C. Friedel, and J.M. Crafts J. Chem. Soc. 32 1877 725
4. G.A. Olah, R. Krishnamurti, and G.K.S. Prakash B.M. Trost, I. Fleming, Friedel-Crafts Alkylations in Comprehensive Organic Synthesis Vol. 3 1991 Pergamon Press Oxford. 293 339
5. For recent reviews on asymmetric F-C reactions catalyzed by metal-complexes, see: K.A. Jørgensen Synthesis 2003 1117
6. M. Bandini, A. Melloni, and A. Umani-Ronchi Angew. Chem., Int. Ed. 43 2004 550
7. M. Bandini, A. Melloni, and A. Umani-Ronchi Synlett 2005 1199
8. T.B. Poulsen, and K.A. Jørgensen Chem. Rev. 108 2008 2903
9. For leading references on asymmetric F-C reactions on silyl enol ethers: A. Ishii, J. Kojima, and K. Mikami Org. Lett. 1 1999 2013
10. For recent reviews on asymmetric F-C reactions using organocatalyst, see: S.B. Tsogoeva Eur. J. Org. Chem. 2007 1701
11. S.-L. You, Q. Cai, and M. Zeng Chem. Soc. Rev. 38 2009 2190
12. M. Zeng, and S.-L. You Synlett 2010 1289
13. V. Terrasson, R.M. de Figueiredo, and J.M. Campagne Eur. J. Org. Chem. 2010 2635
14. Catalytic asymmetric F-C alkylation of indole with activated alkenes, see: K.B. Jensen, J. Thorhauge, R.G. Hazell, and K.A. Jørgensen Angew. Chem., Int. Ed. 40 2001 160
15. W. Zhuang, T. Hansen, and K.A. Jørgensen Chem. Commun. 2001 347
16. D.A. Evans, K.A. Scheidt, K.R. Fandrick, H.W. Lam, and J. Wu J. Am. Chem. Soc. 125 2003 10780
17. J. Zhou, and Y. Tang Chem. Commun. 2004 432
18. R. Rasappan, M. Hager, A. Gissibl, and O. Reiser Org. Lett. 8 2006 6099
19. G. Blay, I. Fernandez, J.R. Pedro, and C. Vila Org. Lett. 9 2007 2601
20. M. Rueping, B.J. Nachtsheim, S.A. Moreth, and M. Bolte Angew. Chem., Int. Ed. 47 2008 593
21. G. Desimoni, G. Faita, M. Toscanini, and M. Boiocchi Chem. Eur. J. 14 2008 3630
22. K. Suyama, K. Matsumoto, and T. Katsuki Heterocycles 77 2009 817
23. L. Hong, C. Liu, W. Sun, L. Wang, K. Wong, and R. Wang Org. Lett. 11 2009 2177
24. A.J. Boersma, B.L. Feringa, and G. Roelfes Angew. Chem., Int. Ed. 48 2009 3346
25. Q. Cai, Z.-A. Zhao, and S.-L. You Angew. Chem., Int. Ed. 48 2009 7428
26. Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, and S.-L. You Chem. Eur. J. 15 2009 3351
27. Y. Liu, D. Shang, X. Zhou, Y. Zhu, L. Lin, X. Liu, and X. Feng Org. Lett. 12 2010 180
28. J. Lv, X. Li, L. Zhong, S. Luo, and J.-P. Cheng Org. Lett. 12 2010 1096
29. C. Zheng, Y.-F. Sheng, Y.-X. Li, and S.-L. You Tetrahedron 66 2010 2875
30. H. Liu, and D.-M. Du Adv. Synth. Catal. 352 2010 1113
31. L. Yang, Q. Zhu, S. Guo, B. Qian, C. Xia, and H. Huang Chem. Eur. J. 16 2010 1638
32. W. Wang, X. Liu, W. Cao, J. Wang, L. Lin, and X. Feng Chem. Eur. J. 16 2010 1664
33. H. Liu, and D.-M. Du Eur. J. Org. Chem. 2010 2121
34. D. Enders, C. Wang, M. Mukanova, and A. Greb Chem. Commun. 2010 2447
35. W. Mei, W. Shoufeng, X. Chungu, and S. Wei Chin. J. Chem. 28 2010 1424
36. S. Jin, C. Li, Y. Ma, Y. Kan, Y.J. Zhang, and W. Zhang Org. Biomol. Chem. 8 2010 4011
37. P. Bachu, and T. Akiyama Chem. Commun. 2010 4112
38. H.Y. Kim, S. Kim, and K. Oh Angew. Chem., Int. Ed. 49 2010 4476
39. T. Sakamoto, J. Itoh, K. Mori, and T. Akiyama Org. Biomol. Chem. 8 2010 5448
40. G. Blay, I. Fernández, M.C. Muñoz, J.R. Pedro, and C. Vila Chem. Eur. J. 16 2010 9117
41. Z.-H. Shi, H. Sheng, K.-F. Yang, J.-X. Jiang, G.-Q. Lai, Y. Lu, and L.W. Xu Eur. J. Org. Chem. 2011 66
42. L. Wen, Q. Shen, X. Wan, and L. Lu J. Org. Chem. 76 2011 2282
43. Catalytic asymmetric F-C alkylation of pyrrole with activated alkenes, see: N.A. Paras, and D.W.C. MacMillan J. Am. Chem. Soc. 123 2001 4370
44. C. Palomo, M. Oiarbide, B.G. Kardak, J.M. Garcia, and A. Linden J. Am. Chem. Soc. 127 2005 4154
45. D.A. Evans, and K.R. Fandrick Org. Lett. 8 2006 2249
46. B.F. Bonini, E. Capitó, M. Comes-Franchini, M. Fochi, A. Ricci, and B. Zwanenburg Tetrahedron: Asymmetry 17 2006 3135
47. D.A. Evans, K.R. Fandrick, H.-J. Song, K.A. Scheidt, and R. Xu J. Am. Chem. Soc. 129 2007 10029
48. B.M. Trost, and C. Müller J. Am. Chem. Soc. 130 2008 2438
49. C.-L. Cao, Y.-Y. Zhou, X.-L. Sun, and Y. Tang Tetrahedron 64 2008 10676
50. H. Liu, S.-F. Lu, J. Xu, and D.-M. Du Chem. Asian J. 3 2008 1111
51. N. Yokoyama, and T. Arai Chem. Commun. 2009 3285
52. S. Yamazaki, S. Kashima, T. Kuriyama, Y. Iwata, T. Morimoto, and K. Kakiuchi Tetrahedron: Asymmetry 20 2009 1224
53. Y.-F. Sheng, Q. Gu, A.-J. Zhang, and S.-L. You J. Org. Chem. 74 2009 6899
54. P.K. Singh, and V.K. Singh Org. Lett. 12 2010 80
55. X. Liang, J. Fan, F. Shi, and W. Su Tetrahedron Lett. 51 2010 2505
56. During the preparation of this manuscript, Kim et al. reported the Pd-catalyzed F-C alkylation of indoles with β,γ-unsaturated α-keto phosphonates as activated alkenes. Y.K. Kang, K.H. Suh, and D.Y. Kim Synlett 2011 1125
57. A. Fürstner Angew. Chem., Int. Ed. 42 2003 3582
58. H. Hoffmann, and T. Lindel Synthesis 2003 1753
59. A. Fürstner, K. Radkowski, and H. Peters Angew. Chem., Int. Ed. 44 2005 2777
60. J.M. Richter, Y. Ishihara, T. Masuda, B.W. Whitefield, T. Llamas, A. Pohjakallio, and P.S. Baran J. Am. Chem. Soc. 130 2008 17938
61. K. Li, and K.K. Hii Chem. Commun. 2003 1132
62. K. Li, X. Cheng, and K.K. Hii Eur. J. Org. Chem. 2004 959
63. P.H. Phua, J.G. de Vries, and K.K. Hill Adv. Synth. Catal. 347 2005 1775
64. K.K. Hii Pure Appl. Chem. 78 2006 341
65. M. Guinó, P.H. Phua, J.-C. Caille, and K.K. Hii J. Org. Chem. 72 2007 6290
66. Y. Hamashima, H. Somei, Y. Shimura, T. Tamura, and M. Sodeoka Org. Lett. 6 2004 1861
67. K. Aikawa, S. Kainuma, M. Hatano, and K. Mikami Tetrahedron Lett. 45 2004 183
68. K. Mikami, Y. Kawakami, K. Akiyama, and K. Aikawa J. Am. Chem. Soc. 129 2007 12950
69. K. Aikawa, Y. Hioki, and K. Mikami J. Am. Chem. Soc. 131 2009 13922
70. K. Aikawa, Y. Hioki, and K. Mikami Chem. Asian J. 5 2010 2346
71. K. Aikawa, Y. Hioki, and K. Mikami Org. Lett. 12 2010 5716
72. K. Aikawa, S. Mimura, Y. Numata, and K. Mikami Eur. J. Org. Chem. 2011 62
73. 2: B.K. Corkey, and F.D. Toste J. Am. Chem. Soc. 127 2005 17168
74. R of minor S-isomer 22.7 min.