Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2726-2729

  Cai, Yunfei ^a   Li, Jun ^a   Chen, Weiliang ^a   Xie, Mingsheng ^a   Liu, Xiaohua ^a   Lin, Lili ^a   Feng, Xiaoming ^a  

^a Sichuan University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; MESYLIC ACID DERIVATIVE; OXINDOLE; SCANDIUM; SCANDIUM TRIFLATE; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDOLES; MESYLATES; MOLECULAR STRUCTURE; SCANDIUM; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 84861799395     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3009446     Document Type: Article

References (50)

1. Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127
2. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945
3. Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36
4. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
5. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
6. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003
7. Zhou, F.; Liu, Y. L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
8. Shen, K.; Liu, X. H.; Lin, L. L.; Feng, X. M. Chem. Sci 2012, 3, 327
9. Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M. J. Am. Chem. Soc. 2005, 127, 10164
10. Shibata, N.; Kohno, J.; Takai, K.; Nakamura, S.; Toru, T.; Kagemasa, S. Angew. Chem., Int. Ed. 2005, 44, 4204
11. Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157
12. Deng, Q.-H.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2011, 17, 14922
13. Wu, L.; Falivene, L.; Drinkel, E.; Grant, S.; Linden, A.; Cavallo, L.; Dorta, R. Angew. Chem., Int. Ed. 2012, 51, 2870
14. Zheng, W. H.; Zhang, Z. H.; Kaplan, M. J.; Antilla, J. C. J. Am. Chem. Soc. 2011, 133, 3339
15. Zhao, M.-X.; Zhang, Z.-W.; Chen, M.-X.; Tang, W.-H.; Shi, M. Eur. J. Org. Chem. 2011, 3001
16. Bui, T.; Borregan, M.; Barbas, C. F., III J. Org. Chem. 2009, 74, 8935
17. Cheng, L.; Liu, L.; Wang, D.; Chen, Y. J. Org. Lett. 2009, 11, 3874
18. Qian, Z. Q.; Zhou, F.; Du, T. P.; Wang, B. L.; Zhou, J. Chem. Commun. 2009, 6753
19. Mouri, S.; Chen, Z.; Mitsunuma, H.; Furutachi, M.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255
20. Yang, Z. G.; Wang, Z.; Bai, S.; Shen, K.; Chen, D. H.; Liu, X. H.; Lin, L. L.; Feng, X. M. Chem.-Eur. J. 2010, 16, 6632
21. Shen, K.; Liu, X. H.; Wang, G.; Lin, L. L.; Feng, X. M. Angew. Chem., Int. Ed. 2011, 50, 4684
22. Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353
23. Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488
24. Sano, D.; Nagata, K.; Itoh, T. Org. Lett. 2008, 10, 1593
25. Itoh, J.; Han, S. B.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 6313
26. Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 6946
27. Itoh, T.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2009, 11, 3854
28. Bui, T.; Candeias, N. R.; Barbas, C. F., III J. Am. Chem. Soc. 2010, 132, 5574
29. Liu, Y.-L.; Wang, B.-L.; Cao, J.-J.; Chen, L.; Zhang, C.; Wang, Y.-X.; Zhou, J. J. Am. Chem. Soc. 2010, 132, 15176
30. Zhang, Z.; Zheng, W.; Antilla, J. C. Angew. Chem., Int. Ed. 2011, 50, 1135
31. Li, Y.; Shi, Y.; Huang, Z.; Wu, X.; Xu, P.; Wang, J.; Zhang, Y. Org. Lett. 2011, 13, 1210
32. England, D. B.; Merey, G.; Padwa, A. Heterocycle 2007, 74, 491
33. Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jøgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794
34. Sobhani, S.; Fielenbach, D.; Marigo, M.; Wabnitz, T. C.; Jøgensen, K. A. Chem.-Eur. J. 2005, 11, 5689
35. Jereb, M.; Togni, A. Org. Lett. 2005, 7, 4041
36. Jereb, M.; Togni, A. Chem.-Eur. J. 2007, 13, 9384
37. Sirisailam, S. K.; Togni, A. Tetrahedron: Asymmetry 2006, 17, 2603-2607
38. Fang, L.; Lin, A.-J.; Hu, H.-W.; Zhu, C.-J. Chem.-Eur. J. 2009, 15, 7039
39. Lin, A.; Fang, L.; Zhu, X.; Zhu, C.; Cheng, Y. Adv. Synth. Catal. 2011, 353, 545
40. Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187
41. Yamamoto, H.; Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924
42. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
43. Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2011, 50, 4760
44. Liu, X. H.; Lin, L. L.; Feng, X. M. Acc. Chem. Res. 2011, 44, 574
45. Malkov, A. V.; Kočovský, P. Eur. J. Org. Chem. 2007, 29
46. CCDC 869058 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambrige Crystallographic Data Centere via www.ccdc.cam.ac.uk/data-request/cif.
47. Wabnitz, T. C.; Yu, J.-Q.; Spencer, J. B. Chem.-Eur. J. 2004, 10, 484
48. Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem., Int. Ed. 2002, 41, 3554
49. For a review on nonlinear effects, see: Satyanarayana, T.; Abraham, S.; Kagan, H. B. Angew. Chem., Int. Ed. 2009, 48, 456
50. Liu, Y. L.; Shang, D. J.; Zhou, X.; Liu, X. H.; Feng, X. M. Chem.-Eur. J. 2009, 15, 2055