Enantioselective Friedel-Crafts alkylation of indoles with β,γ-unsaturated α-ketoesters catalyzed by new squaramide-linked bisoxazoline-Zn(OTf)2 complexes

Tetrahedron Asymmetry

Volumn 25, Issue 13-14, 2014, Pages 980-988

  Jia, Sheng Jian ^a   Du, Da Ming ^a  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BETA,GAMMA UNSATURATED ALPHA KETOESTER; ESTER; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL;

EID: 84905018175     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2014.05.011     Document Type: Article

References (68)

1. For recent reviews on asymmetric Friedel-Crafts alkylation reactions, see: T.B. Poulsen, and K.A. Jørgensen Chem. Rev. 108 2008 2903
2. K.A. Jørgensen Synthesis 7 2003 1117
3. M. Bandini, A. Melloni, and A. Umani-Ronchi Angew. Chem., Int. Ed. 43 2004 550
4. M. Bandini, A. Melloni, S. Tommasi, and A. Umani-Ronchi Synlett 2005 1199
5. M. Bandini, P.G. Cozzi, P. Melchiorre, and A. Umani-Ronchi Angew. Chem., Int. Ed. 43 2004 84
6. D. Almasi, D. Alonso, and A.C. Nájera Tetrahedron: Asymmetry 18 2007 299
7. M. Bandini, and A. Eichholzer Angew. Chem., Int. Ed. 48 2009 9608
8. S.-L. You, Q. Cai, and M. Zeng Chem. Soc. Rev. 38 2009 2190
9. For selected examples of asymmetric Friedel-Crafts alkylations, see: R.P. Herrera, V. Sgarzani, L. Bernardi, and A. Ricci Angew. Chem., Int. Ed. 44 2005 6576
10. Y.-X. Jia, S.-F. Zhu, Y. Yang, and Q.-L. Zhou J. Org. Chem. 71 2006 75
11. S.-F. Lu, D.-M. Du, and J. Xu Org. Lett. 8 2006 2115
12. H. Liu, J. Xu, and D.-M. Du Org. Lett. 9 2007 4725
13. H. Liu, S.-F. Lu, J. Xu, and D.-M. Du Chem. Asian J. 3 2008 1111
14. G. Madhu, and S. Daniel J. Am. Chem. Soc. 130 2008 16464
15. T. Akiyama, K. Fuchibe, and J. Itoh Angew. Chem., Int. Ed. 47 2008 4016
16. B.M. Trost, and C. Mueller J. Am. Chem. Soc. 130 2008 2438
17. Y.-F. Sheng, Q. Gu, A.-J. Zhang, and S.-L. You J. Org. Chem. 74 2009 6899
18. S.C. McKeon, H. Müeller-Bunz, and P.J. Guiry Eur. J. Org. Chem. 2009 4833
19. N. Yokoyama, and T. Arai Chem. Commun. 2009 3285
20. H. Liu, and D.-M. Du Adv. Synth. Catal. 352 2010 1113
21. H. Liu, and D.-M. Du Eur. J. Org. Chem. 2010 2121
22. Y. Sohtome, B. Shin, N. Horitsugi, R. Takagi, K. Noguchi, and K. Nagasawa Angew. Chem., Int. Ed. 49 2010 7299
23. E. Marques-Lopez, A. Alcaine, T. Tejeo, and R.P. Herrera Eur. J. Org. Chem. 2011 3700
24. K.C. Nicolaou, and S.A. Snyder Classics in Total Synthesis II 2003 Wiley-VCH Weinheim
25. H.J. Borschberg Curr. Org. Chem. 9 2005 1465
26. A. Kleeman, J. Engel, B. Kutscher, and D. Reichert Pharmaceutical Substances 4th ed. 2001 Thieme New York
27. D.J. Rawson, K.N. Dack, R.P. Dickinson, and K. James Bioorg. Med. Chem. Lett. 12 2002 125
28. A.C. Kinsman, and M.A. Kerr J. Am. Chem. Soc. 125 2003 14120
29. J. Chang-Fang, J.B. Rangisetty, M. Dukat, V. Setola, T. Raffay, B. Roth, and R.A. Glennon Bioorg. Med. Chem. Lett. 14 2004 1961
30. M. Rueping, B.J. Nachtsheim, S.A. Moreth, and M. Bolte Angew. Chem., Int. Ed. 47 2008 593
31. K.B. Jensen, J. Thorhauge, R.G. Hazell, and K.A. Jørgensen Angew. Chem., Int. Ed. 40 2001 160
32. G. Desimoni, G. Faita, M. Toscanini, and M. Boiocchi Chem. Eur. J. 14 2008 3630
33. Y.-L. Liu, D.-J. Shang, X. Zhou, Y. Zhu, L.-L. Lin, X.-H. Liu, and X.-M. Feng Org. Lett. 12 2010 180
34. J. Lv, X. Li, L. Zhong, S.Z. Luo, and J.-P. Cheng Org. Lett. 12 2010 1096
35. L. Liu, H. Ma, Y. Xiao, F. Du, Z. Qin, N. Li, and B. Fu Chem. Commun. 2012 9281
36. For examples, see: D. Popa, C. Puigjaner, M. Gómez, J. Benet-Buchholz, A. Vidal-Ferran, and M.A. Pericàs Adv. Synth. Catal. 349 2007 2265
37. M. Dieguez, and O. Pamies Chem. Eur. J. 14 2008 3653
38. J. Velder, T. Robert, I. Weidner, J.-M. Neudoerfl, J. Lex, and H.-G. Schmalz Adv. Synth. Catal. 350 2008 1309
39. B.K. Langlotz, H. Wadepohl, and L.H. Gade Angew. Chem., Int. Ed. 47 2008 4670
40. H. Fernandez-Perez, M.A. Pericàs, and A. Vidal-Ferran Adv. Synth. Catal. 350 2008 1984
41. B.-G. Zhao, J.-J. Liang, J. Yang, C.-D. Jia, X.-J. Yang, H.-R. Zhang, N. Tang, and C. Janiak Chem.-Eur. J. 14 2008 7847
42. U. Nagel, and C. Diez Eur. J. Inorg. Chem. 2009 1248
43. D. Popa, R. Marcos, S. Sayalero, A. Vidal-Ferran, and M.A. Pericàs Adv. Synth. Catal. 351 2009 1539
44. For selected recent reviews, see: J.S. Johnson, and D.A. Evans Acc. Chem. Res. 33 2000 325
45. D. Rechavi, and M. Lemaire Chem. Rev. 102 2002 3467
46. G. Desimoni, G. Faita, and P. Quadrelli Chem. Rev. 103 2003 3119
47. J. Zhou, and Y. Tang Chem. Soc. Rev. 34 2005 664
48. G. Desimoni, G. Faita, and K.A. Jørgensen Chem. Rev. 106 2006 3561
49. H. Nishiyama Chem. Soc. Rev. 36 2007 1133
50. G.C. Hargaden, and P.J. Guiry Chem. Rev. 109 2009 2505
51. M. Gómez, S. Jansat, G. Muller, M.A. Maestro, and J. Mahía Organometallics 21 2002 1077
52. X. Du, H. Liu, and D.-M. Du Tetrahedron: Asymmetry 21 2010 241
53. Y. Jin, and D.M. Du Tetrahedron 68 2012 3633
54. T. Yamagishi, M. Ohnuki, T. Kiyooka, D. Masui, K. Sato, and M. Yamaguchi Tetrahedron: Asymmetry 14 2003 3275
55. P. Braunstein, F. Naud, A. Pfaltz, and S.J. Rettig Organometallics 19 2000 2676
56. M.R. Castillo, S. Castillón, C. Claver, J.M. Fraile, A. Gual, M. Martín, J.A. Mayoral, and E. Sola Tetrahedron 67 2011 5402
57. For selected examples of asymmetric reactions using squaramides, see: J.P. Malerich, K. Hagihara, and V.H. Rawal J. Am. Chem. Soc. 130 2008 14416
58. Y. Zhu, J.P. Malerich, and V.H. Rawal Angew. Chem., Int. Ed. 49 2010 153
59. D.Q. Xu, Y.-F. Wang, W. Zhang, S.-P. Luo, A.-G. Zhong, A.-B. Xia, and Z.-Y. Xu Chem.-Eur. J. 16 2010 4177
60. Y. Qian, G. Ma, A. Lv, H.-L. Zhu, J. Zhao, and V.H. Rawal Chem. Commun. 2010 3004
61. H. Konishi, T.Y. Lam, J.P. Malerich, and V.H. Rawal Org. Lett. 12 2010 2028
62. W. Yang, and D.-M. Du Org. Lett. 12 2010 5450
63. S.V. Pansare, and E.K. Paul Chem. Commun. 2011 1027
64. W. Yang, and D.-M. Du Adv. Synth. Catal. 353 2011 1241
65. W. Yang, and D.-M. Du Chem. Commun. 2011 12706
66. C. Min, X. Han, Z.Q. Liao, X.F. Wu, H.-B. Zhou, and C. Dong Adv. Synth. Catal. 353 2011 2715
67. H.Y. Bae, S. Some, J.H. Lee, J.-Y. Kim, M.J. Song, S. Lee, Y.J. Zhang, and C.E. Song Adv. Synth. Catal. 353 2011 3196
68. P. Västilä, I.M. Pastor, and H. Adolfsson J. Org. Chem. 70 2005 2921