Cinchonidine thiourea catalyzed asymmetric addition of phenols to oxindole derivatives

RSC Advances

Volumn 4, Issue 107, 2014, Pages 62367-62374

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

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FRIEDEL-CRAFTS REACTION; PHENOLS; THIOUREAS;

ASYMMETRIC ADDITION; ENANTIOSELECTIVE; ISATIN DERIVATIVES; ORGANOCATALYSTS;

ENANTIOSELECTIVITY;

EID: 84912141079     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra09805f     Document Type: Article

References (47)

1. (a) R. Dalpozzo, G. Bartoli and G. Bencivenni, Chem. Soc. Rev., 2012, 41, 7247-7290;
2. (b) F. Zhou, Y.-L. Liu and J. Zhou, Adv. Synth. Catal., 2010, 352, 1381;
3. (c) S. Peddibhotla, Curr. Bioact. Compd., 2009, 5, 20;
4. (d) C. V. Galliford and K. A. Scheidt, Angew. Chem., Int. Ed., 2007, 46, 8748;
5. (e) C. Marti and E. M. Carreira, Eur. J. Org. Chem., 2003, 2209;
6. (f) H. Lin and S. J. Danishefsky, Angew. Chem., Int. Ed., 2003, 42, 36;
7. (g) S. Hibino and T. Choshi, Nat. Prod. Rep., 2001, 18, 66;
8. (h) Y.-Q. Tang, I. Sattler, R. Thiericke, S. Grabley and X.-Z. Feng, Eur. J. Org. Chem., 2001, 261;
9. (i) B. S. Jensen, CNS Drug Rev., 2002, 8, 353;
10. (j) Y. Koguchi, J. Kohno, M. Nishio, K. Takahashi, T. Okuda, T. Ohnuki and S. Komatsubara, J. Antibiot., 2000, 53, 105.
11. (a) S. Chowdhury, M. Chafeev, S. Liu, J. Sun, V. Raina, R. Chui, W. Young, R. Kwan, J. Fu and J. A. Cadieux, Bioorg. Med. Chem. Lett., 2011, 21, 3676;
12. (b) 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., 2001, 44, 4641;
13. (c) Y.-Q. Tang, I. Sattler, R. Thiericke and S. Grabley, Eur. J. Org. Chem., 2001, 66, 261;
14. (d) J. Nagamine, R. Nagata, H. Seki, N. Nomura-Akimaru, Y. Ueki, K. Kumagai, M. Taiji and H. Noguchi, J. Endocrinol., 2001, 171, 481;
15. (e) Y. Kamano, H.-P. Zhang, Y. Ichihara, H. Kizu, K. Komiyama and G. R. Pettit, Tetrahedron Lett., 1995, 36, 2783;
16. (f) J.-J. Cadieux, M. Chafeev, S. Chowdhury, J. Fu, Q. Jia, S. Abel, E. Al-Sayed, E. Huthmann and T. Isarno, US Patent 2013/0072686, 2013;
17. (g) M. Chafeev, J. Fu and J.-J. Cadieux, US Patent 2013/0072537, 2013;
18. (h) A. Di Malta, G. Garcia, R. Roux, B. Schoentjes, C. Serradeil-le Gal, B. Tonnerre and J. Wagnon, PCT Int. Appl. No. WO2003008407, 2003.
19. (a) A. Kumar and S. S. Chimni, RSC Adv., 2012, 2, 9748.
20. (b) S. Mohammadi, R. Heiran, R. P. Herrera and E. Marqués-López, ChemCatChem, 2013, 5, 2131;
21. (c) M. Flores, J. Pena, P. García-García, N. M. Garrido and D. Diez, Curr. Org. Chem., 2013, 17, 1957.
22. (d) T. Ishimaru, N. Shibata, J. Nagai, S. Nakamura, T. Toru and S. Kanemasa, J. Am. Chem. Soc., 2006, 128, 16488;
23. (e) Z. Zhang, W. Zheng and J. C. Antilla, Angew. Chem., Int. Ed., 2011, 50, 1135;
24. (f) Y.-X. Jia, J. M. Hillgren, E. L. Watson, S. P. Marsden and E. P. Kundig, Chem. Commun., 2008, 4040.
25. (a) D. Tomita, K. Yamatsugu, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2009, 131, 6946;
26. (b) N. V. Hanhan, A. H. Sahin, T. W. Chang, J. C. Fettinger and A. K. Franz, Angew. Chem., Int. Ed., 2010, 49, 744;
27. (c) E. G. Gutierrez, C. J. Wong, A. H. Sahin and A. K. Franz, Org. Lett., 2011, 13, 5754.
28. (d) R. Shintani, M. Inoue and T. Hayashi, Angew. Chem., Int. Ed., 2006, 45, 3353;
29. (e) P. Y. Toullec, R. B. C. Jagt, J. G. de Vries, B. L. Feringa and A. J. Minnaard, Org. Lett., 2006, 8, 2715;
30. (f) X. Feng, Y. Nie, J. Yang and H. Du, Org. Lett., 2012, 14, 624;
31. (g) J. Gui, G. Chen, P. Cao and J. Liao, Tetrahedron: Asymmetry, 2012, 23, 554;
32. (h) H. Lai, Z. Huang, Q. Wu and Y. Qin, J. Org. Chem., 2009, 74, 283;
33. (i) Z. Liu, P. Gu, M. Shi, P. McDowell and G. Li, Org. Lett., 2011, 13, 2314.
34. (a) P. Chauhan and S. S. Chimni, Chem.-Eur. J., 2010, 26, 7709;
35. (b) J. Deng, S. Zhang, P. Ding, H. Jiang, W. Wang and J. Li, Adv. Synth. Catal., 2010, 352, 833.
36. (a) J. Kaur, A. Kumar and S. S. Chimni, Tetrahedron Lett., 2014, 55, 2138;
37. (b) A. Kumar, J. Kaur, P. Chauhan and S. S. Chimni, Chem.-Asian J., 2014, 9, 1305;
38. (c) D. Wu, X. Zhang, Y. Xu, Y. Xue, J. Li, W. Wang and J. Zhu, Asian J. Org. Chem., 2014, 3, 480.
39. (a) G. X. Li and J. Qu, Chem. Commun., 2012, 48, 5518;
40. (b) S. Bai, X. Liu, Z. Wang, W. Cao and L. Lin, Adv. Synth. Catal., 2012, 354, 2096;
41. (c) Y. Sohtome, B. Shin, N. Horitsugi, R. Takagi, K. Noguchi and K. Nagasawa, Chem.-Asian J., 2010, 122, 7457;
42. (d) J.-L. Zhao, L. Liu, C.-L. Gu, D. Wang and Y.-J. Chen, Tetrahedron Lett., 2008, 49, 1476.
43. (a) P. Hewawasam, M. Erway, S. L. Moon, J. Knipe, H. Weiner, C. G. Boissard, D. J. Post-Munson, Q. Gao, S. Huang, V. K. Gribkoff and N. A. Meanwell, J. Med. Chem., 2002, 45, 1487;
44. (b) T. Tokunaga, W. E. Hume, J. Nagamine, T. Kawamura, M. Taiji and R. Nagata, Bioorg. Med. Chem. Lett., 2005, 15, 1789.
45. (a) A. Kumar and S. S. Chimni, Eur. J. Org. Chem., 2013, 4780;
46. (b) A. Kumar and S. S. Chimni, Tetrahedron, 2013, 69, 5197;
47. (c) P. Chauhan and S. S. Chimni, Asian J. Org. Chem., 2013, 2, 533.