Highly enantioselective and organocatalytic α-amination of 2-Oxindoles

Organic Letters

Volumn 11, Issue 17, 2009, Pages 3874-3877

  Cheng, Liang ^a,b   Liu, Li ^a,b   Wang, Dong ^a,b   Chen, Yong Jun ^a,b  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; OXINDOLE;

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

AMINATION; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 69449091605     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901405r     Document Type: Article

References (53)

1. Brown, R. T. In The Chemistry of Heterocyclic Compounds, Part 4. Indoles: The Monoterpenoid Indole Alkaloids; Saxton, J. E., Eds.; John Wiley and Sons: New York, 1983; Vol. 25.
2. (a) Ochi, M.; Kawasaki, Y.; Kataoka, H.; Uchio, Y. Biochem. Biophys. Res. Commun. 2001, 283, 1118.
3. (b) Bernard, K.; Bogliolo, S.; Ehrenfeld, J. Br. J. Pharmacol. 2005, 144, 1037.
4. (c) Chen, L.; Yang, S.; Zhang, J.; Zhang, Z. U. S. Patent 81810 Al, 2008.
5. (a) Marsden, S. P.; Watson, E. L.; Sraw, S. A. Org. Lett. 2008, 10, 2905.
6. (b) Watson, E. L.; Marsden, S. P.; Raw, S. A. Tetrahedron Lett. 2009, 50, 3318.
7. (c) Jia, Y.-X.; Hillgren, J. M.; Watson, E. L.; Marsden, S. P.; Kündig, E. P. Chem. Commun. 2008, 4040.
8. For selected examples, see: (a) Emura, T.; Esaki, T.; Tachibana, K.; Shimizu, M. J. Org. Chem. 2006, 71, 8559.
9. (b) Sun, C.; Lin, X.; Weinreb, S. M. J. Org. Chem. 2006, 71, 3159.
10. (c) Magnus, P.; Turnbull, R. Org. Lett. 2006, 8, 3497.
11. (d) Miyabe, H.; Yamaoka, Y.; Takemoto, Y. J. Org. Chem. 2005, 70, 3324.
12. (e) Lesma, G.; Landoni, N.; Pilati T.; Sacchetti, A.; Silvani, A. J. Org. Chem. 2009, 74, 4537.
13. For selected examples, see: (a) Bella, A. F.; Slawin, A. M. Z.; Walton, J. C. J. Org. Chem. 2004, 69, 5926.
14. (b) O'Connor, S. J.; Liu, Z. Synlett 2003, 14, 2135.
15. Aldol and Mannich reactions of oxindoles: (a) Ogawa, S.; Shibata, N.; Inagaki, J.; Nakamura, S.; Toru, T.; Shiri, M. Angew. Chem., Int. Ed. 2007, 46, 8666.
16. (b) Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008, 10, 3583.
17. (c) He, R.; Ding, C.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48, 4559.
18. (d) Cheng, L.; Liu, L.; Jia, H.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2009, 74, 4650. Michael addition:
19. (e) Galzerano, P.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem.-Eur. J. [Online early access]. DOI: 10.1002/chem.200802466. Published Online: Jan 29, 2009.
20. (f) Bui, T.; Syed, S.; Barbas, C. F., III. J. Am. Chem. Soc. 2009, 131, 8758.
21. (g) Kato, Y.; Furutachi, M.; Chen, Z.; Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168, and ref 6c Allylation:
22. (h) Trost, B. M.; Frederiksen, M. U. Angew. Chem., Int. Ed. 2005, 44, 308.
23. (i) Trost, B. M.; Zhang, Y. J. Am. Chem. Soc. 2006, 128, 4590.
24. (j) Trost, B. M.; Zhang, Y. J. Am. Chem. Soc. 2007, 129, 14548.
25. (k) Jiang, K.; Peng, J.; Cui, H.-L.; Chen, Y.-C. Chem. Commun. 2009, 3955.
26. For recent examples of fluorination and hydroxylation of 2-oxindoles, see: (a) Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157.
27. (b) Sano, D.; Nagata, K.; Itoh, T. Org. Lett. 2008, 10, 1593.
28. (a) Genet, J.-P.; Creek, C.; Lavergne, D. In Modern Amination Methods; Ricci, A., Eds.; Wiley-VCH: Weinheim, 2000; Chapter 3.
29. (b) Janey, J. M. Angew. Chem., Int. Ed. 2005, 44, 4292.
30. For examples of catalytic asymmetric α-amination using cinchona alkaloids catalysts, see: (a) Saaby, S.; Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120.
31. (b) Pihko, P. M.; Pohjakallio, A. Synlett 2004, 2115.
32. (c) Poulsen, T. B.; Alemparte, C.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 11614.
33. (d) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167.
34. (e) Liu, T.-Y.; Cui, H.-L.; Zhang, Y.; Jiang, K.; Du, W.; He, Z.-Q.; Chen, Y.-C. Org. Lett. 2007, 9, 3671.
35. For selected examples of catalytic asymmetric α-amination using other organocatalysts, see: (a) List, B. J. Am. Chem. Soc. 2002, 124, 5656.
36. (b) Suri, J. T.; Steiner, D. D.; Barbas, C. F., III. Org. Lett. 2005, 7, 3885.
37. (c) Franzn, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296.
38. (d) Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128, 16044.
39. (e) Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659.
40. (f) He, R.; Wang, X.; Hashimoto, T.; Maruoka, K. Angew. Chem., Int. Ed. 2008, 47, 9466.
41. For a few reported catalytic asymmetric reaction using N-H 2-oxindoles, see ref 6a,d,e.
42. For reviews on modified cinchona alkaoids, see: (a) Kacprzak, K.; Gawroňski, J. Synthesis 2001, 961.
43. (b) Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621. For some pioneering work using biscinchona alkaloids, see:
44. (c) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195.
45. (d) McDaid, P.; Chen, Y.; Deng, L. Angew. Chem., Int. Ed. 2002, 41, 338.
46. (e) Tian, S.-K.; Hong, R.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
47. See the Supporting Information for details.
48. For recent examples in which the N-H of indole plays a crucial role, see: (a) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 6576.
49. (b) Jia, Y.-X.; Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2007, 46, 5565.
50. (a) Dijkstra, G. D. H.; Kellog, R. M.; Wynberg, H.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069.
51. (b) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1993, 115, 12579.
52. (c) Corey, E. J.; Noe, M. C. J. Am Chem. Soc. 1996, 118, 11038.
53. (d) Marko, I. E.; Svendsen, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Heidelberg, 2000; Chapter 20.