Organocatalytic asymmetric Friedel-Crafts reaction of 1-naphthols with isatins: An enantioselective synthesis of 3-aryl-3-hydroxy-2-oxindoles

Tetrahedron Letters

Volumn 55, Issue 13, 2014, Pages 2138-2141

  Kaur, Jasneet ^a   Kumar, Akshay ^a   Chimni, Swapandeep Singh ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

3 Hydroxyoxindoles; Cinchona thioureas; Friedel Crafts reaction; Isatins; Organocatalysis

Indexed keywords

1 NAPHTHOL; 3 ARYL 3 HYDROXY 2 OXINDOLE DERIVATIVE; ISATIN; OXINDOLE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION;

EID: 84896515005     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.02.054     Document Type: Article

References (72)

1. G.A. Olah Friedel-Crafts and Related Reactions Vols. 1-4 1963-65 Wiley-Interscience New York
2. G.A. Olah, R. Krishnamurti, and G.K.S. Prakash B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 3 1991 Pergamon Press Oxford 293
3. For selected manuscript, see; (c) M. Bandini, and A. Umani-Ronchi Catalytic Asymmetric Friedel-Crafts Alkylations 2009 Wiley-VCH Weinheim
4. T.B. Poulsen, and K.A. Jørgensen Chem. Rev. 108 2008 2903
5. M. Bandini, A. Melloni, and A. Umani-Ronchi Angew. Chem., Int. Ed. 43 2004 550
6. M. Bandini, A. Melloni, S. Tommasi, and A. Umani-Ronchi Synlett 2005 1199
7. K.A. Jørgensen Synthesis 2003 1117
8. For recent reviews on organocatalytic asymmetric Friedel-Crafts reaction, see: S.-L. You, Q. Cai, and M. Zeng Chem. Soc. Rev. 38 2009 2190
9. V. Terrasson, R.M. de Figueiredo, and J.M. Campagne Eur. J. Org. Chem. 2010 2635
10. M. Zen, and S.-L. You Synlett 2010 1289
11. P. Chauhan, and S.S. Chimni RSC Adv. 2 2012 6117
12. For recent publications, see: P. Chauhan, and S.S. Chimni Tetrahedron Lett. 54 2013 4613
13. G.-X. Li, and J. Qu Chem. Commun. 2012 5518
14. For selected examples, see; (a) J. Itoh, K. Fuchibe, and T. Akiyama Angew. Chem., Int. Ed. 47 2008 4016
15. H.-Y. Tang, A.D. Lu, Z.-H. Zhou, G.-F. Zhao, L.-N. He, and C.-C. Tang Eur. J. Org. Chem. 5 2008 1406
16. R.P. Herrera, V. Sgarzani, L. Bernardi, and A. Ricci Angew. Chem., Int. Ed. 44 2005 6576
17. X.-F. Wang, J.-R. Chen, Y.-J. Cao, H.-G. Cheng, and W.-J. Xiao Org. Lett. 12 2010 1140
18. Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, and S.-L. You Chem. Eur. J. 15 2009 3351
19. M. Rueping, B.J. Nachtsheim, S.A. Moreth, and M. Bolte Angew. Chem., Int. Ed. 47 2008 593
20. I.T. Raheem, P.S. Thiara, and E.N. Jacobsen Org. Lett. 10 2008 1577
21. D. Uraguchi, K. Sorimachi, and M. Terada J. Am. Chem. Soc. 126 2004 11804
22. K.B. Jensen, J. Thorhauge, R.G. Hazell, and K.A. Jørgensen Angew. Chem., Int. Ed. 40 2001 160
23. J. Zhou, and Y. Tang J. Am. Chem. Soc. 124 2002 9030
24. C. Palomo, M. Oiarbide, B.G. Kardak, J.M. GarcIa, and A. Linden J. Am. Chem. Soc. 127 2005 4154
25. D.A. Evans, K.R. Fandrick, and H.J. Song J. Am. Chem. Soc. 127 2005 8942
26. J.L. Zhao, L. Liu, Y. Sui, Y.L. Liu, D. Wang, and Y.J. Chen Org. Lett. 8 2006 6127
27. N.A. Paras, and D.W.C. MacMillan J. Am. Chem. Soc. 123 2001 4370
28. M. Terada, and K. Sorimachi J. Am. Chem. Soc. 129 2007 292
29. Q. Kang, Z.A. Zhao, and S.L. You J. Am. Chem. Soc. 129 2007 1484
30. W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.S. Ding, and Y.C. Chen Org. Biomol. Chem. 5 2007 816
31. J.F. Austin, and D.W.C. MacMillan J. Am. Chem. Soc. 124 2002 1172
32. N.A. Paras, and D.W.C. MacMillan J. Am. Chem. Soc. 124 2002 7894
33. For selected examples of naphthols in asymmetric Friedel-Crafts reaction, see: S. Brandes, M. Bella, A. Kjærsgaard, and K.A. Jorgensen Angew. Chem., Int. Ed. 45 2006 1147
34. T.Y. Liu, H.L. Cui, Q. Chai, J. Long, B.J. Li, Y. Wu, L.S. Ding, and Y.C. Chen Chem. Commun. 2007 2228
35. X. Jiang, L. Wu, Y. Xing, L. Wang, S. Wang, Z. Chen, and R. Wang Chem. Commun. 2012 446
36. X.-S. Wang, C.-W. Zheng, S.-L. Zhao, Z. Chai, G. Zhao, and G.-S. Yang Tetrahedron: Asymmetry 19 2008 2699
37. S. Brandes, M. Bella, A. Kjærsgaard, and K.A. Jørgensen Angew. Chem., Int. Ed. 45 2006 1147
38. S. Brandes, B. Niess, B. Marco, A. Prieto, J. Overgaard, and K.A. Jørgensen Chem. Eur. J. 12 2006 6039
39. T.-Y. Liu, H.-L. Cui, Q. Chai, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, and Y.-C. Chen Chem. Commun. 2007 2228
40. L. Hong, L. Wang, W. Sun, K. Wong, and R. Wang J. Org. Chem. 74 2009 6881
41. P. Chauhan, and S.S. Chimni Eur. J. Org. Chem. 2011 1636
42. G. Liu, S. Zhang, T. Zhang, and W. Wang Org. Lett. 13 2011 828
43. G.S. Singh, and Z.Y. Desta Chem. Rev. 112 2012 6104
44. For recent review on catalytic asymmetric synthesis of 3-substituted 3-hydroxy-2-oxindoles: see; A. Kumar, and S.S. Chimni RSC Adv. 2 2012 9748
45. S. Mohammadi, R. Heiran, R.P. Herrera, and E. Marqués-López ChemCatChem 5 2013 2131 2148
46. M. Flores, J. Pena, P. García-García, N.M. Garrido, and D. Diez Curr. Org. Chem. 17 2013 1957 1985 Publications from our group on chiral 3-hydroxyoxindoles
47. P. Chauhan, and S.S. Chimni Asian J. Org. Chem. 2 2013 586
48. A. Kumar, and S.S. Chimni Eur. J. Org. Chem. 2013 4780
49. A. Kumar, and S.S. Chimni Tetrahedron 69 2013 5197
50. For representative examples, see: T. Tokunaga, W.E. Hume, T. Umezome, K. Okazaki, Y. Ueki, K. Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji, H. Noguchi, and R. Nagata J. Med. Chem. 44 2001 4641
51. M. Kitajima, I. Mori, K. Arai, N. Kogure, and H. Takayama Tetrahedron Lett. 47 2006 3199
52. C.V. Galliford, and K.A. Scheidt Angew. Chem., Int. Ed. 46 2007 8748
53. C. Marti, and E.M. Carreira Eur. J. Org. Chem. 2003 2209
54. Y. Kamano, H.-P. Zhang, Y. Ichihara, H. Kizu, K. Komiyama, and G.R. Pettit Tetrahedron Lett. 36 1995 2783
55. H.-P. Zhang, Y. Kamano, Y. Ichihara, H. Kizu, K. Komiyama, H. Itokawa, and G.R. Pettit Tetrahedron 51 1995 5523
56. Y.-Q. Tang, I. Sattler, R. Thiericke, and S. Grabley Eur. J. Org. Chem. 66 2001 261
57. For selected examples, see; (a) R. Shintani, M. Inoue, and T. Hayashi Angew. Chem., Int. Ed. 45 2006 3353
58. P.Y. Toullec, R.B.C. Jagt, J.G. de Vries, B.L. Feringa, and A.J. Minnaard Org. Lett. 8 2006 2715
59. X. Feng, Y. Nie, J. Yang, and H. Du Org. Lett. 14 2012 624
60. J. Gui, G. Chen, P. Cao, and J. Liao Tetrahedron: Asymmetry 23 2012 554
61. H. Lai, Z. Huang, Q. Wu, and Y. Qin J. Org. Chem. 74 2009 283
62. Z. Liu, P. Gu, M. Shi, P. McDowell, and G. Li Org. Lett. 13 2011 2314
63. D. Tomita, K. Yamatsugu, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 131 2009 6946
64. N.V. Hanhan, A.H. Sahin, T.W. Chang, J.C. Fettinger, and A.K. Franz Angew. Chem., Int. Ed. 49 2010 744
65. E.G. Gutierrez, C.J. Wong, A.H. Sahin, and A.K. Franz Org. Lett. 13 2011 5754
66. T. Ishimaru, N. Shibata, J. Nagai, S. Nakamura, T. Toru, and S. Kanemasa J. Am. Chem. Soc. 128 2006 16488
67. L. Yin, M. Kanai, and M. Shibasaki Angew. Chem., Int. Ed. 50 2011 7620
68. Y.-X. Jia, J.M. Hillgren, E.L. Watson, S.P. Marsden, and E.P. Kundig Chem. Commun. 2008 4040
69. P. Chauhan, and S.S. Chimni Chem. Eur. J. 16 2010 7709
70. J. Deng, S. Zhang, P. Ding, H. Jiang, W. Wang, and J. Li Adv. Synth. Catal. 352 2010 833
71. In 2007, Ramachary et al. reported the non-asymmetric Friedel-Crafts reaction of 2-naphthols with isatins D.B. Ramachary, G.B. Reddy, and R. Mondal Tetrahedron Lett. 48 2007 7618
72. At the time of submission of our manuscript virtually identical reaction was reported by Zhu and co-workers: D. Wu, X. Zhang, Y. Xu, Y. Xue, J. Li, W. Wang, and J. Zhu Asian J. Org. Chem. 2013 10.1002/ajoc.201300170