Construction of the N1-C3 linkage stereogenic centers by catalytic asymmetric amination reaction of 3-bromooxindoles with indolines

Organic Letters

Volumn 16, Issue 9, 2014, Pages 2394-2397

  Zhang, Hailong ^a   Kang, Hong ^a   Hong, Liang ^a   Dong, Weiping ^a   Li, Guolin ^a   Zheng, Xin ^a   Wang, Rui ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID; INDOLE DERIVATIVE; INDOLINE; OXINDOLE; PSYCHOTRIMINE;

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

AMINATION; CATALYSIS; INDOLE ALKALOIDS; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84899881780     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5007423     Document Type: Article

References (63)

1. Anthoni, U.; Christophersen, C.; Nielsen, P. H. Naturally Occurring Cyclotryptophans and Cyclotryptamines. In Alkaloids: Chemical Biological & Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, U.K., 1999; Vol. 13, pp 163-236.
2. Julian, P. L.; Pikl, J. J. Am. Chem. Soc. 1933, 55, 2105
3. Julian, P. L.; Pikl, J.; Boggess, D. J. Am. Chem. Soc. 1934, 56, 1797
4. Julian, P. L.; Pikl, J. J. Am. Chem. Soc. 1935, 57, 755
5. Cordell, G. A.; Saxton, J. E. In The Alkaloids; Elsevier: Amsterdam, 1981; Vol. 20, p 10.
6. Steven, A.; Overman, L. E. Angew. Chem., Int. Ed. 2007, 46, 5488
7. Schmidt, M. A.; Movassaghi, M. Synlett 2008, 3, 313
8. Ruiz-Sanchis, P.; Savina, S. A.; Albericio, F.; Alvarez, M. Chem.-Eur. J. 2011, 17, 1388
9. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945
10. Kodanko, J. J.; Overman, L. E. Angew. Chem., Int. Ed. 2003, 42, 2528
11. Austin, J. F.; Kim, S.-G; Sinz, C. J.; Xiao, W.-J.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482
12. Menozzi, C.; Dalko, P. I.; Cossy, J. Chem. Commun. 2006, 42, 4638
13. Movassaghi, M.; Schmidt, M. A. Angew. Chem., Int. Ed. 2007, 46, 3725
14. Kim, J.; Ashenhurst, J. A.; Movassaghi, M. Science 2009, 324, 238
15. Repka, L. M.; Reisman, S. E. J. Org. Chem. 2013, 78, 12314
16. Kieffer, M. E.; Chuang, K. V.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 5557
17. Repka, L. M.; Ni, J.; Reisman, S. E. J. Am. Chem. Soc. 2010, 132, 14418
18. Waksman, S. A.; Bugie, E. J. Bacteriol. 1944, 48, 527
19. Geiger, W. B.; Conn, J. E.; Waksman, S. A. J. Bacteriol. 1944, 48, 531
20. McInnes, A. G.; Taylor, A.; Walter, J. A. J. Am. Chem. Soc. 1976, 98, 6741
21. Brewer, D.; McInnes, A. G.; Smith, D. G.; Taylor, A.; Walter, J. A.; Loosli, H. R.; Kis, Z. L. J. Chem. Soc., Perkin Trans. 1 1978, 10, 1248
22. Nakao, Y.; Yeung, B. K. S.; Yoshida, W. Y.; Scheuer, P. J.; Kelly-Borges, M. J. Am. Chem. Soc. 1995, 117, 8271
23. Yeung, B. K. S.; Nakao, Y.; Kinnel, R. B.; Carney, J. R.; Yoshida, W. Y.; Scheuer, P. J.; Kelly-Borges, M. J. Org. Chem. 1996, 61, 7168
24. Nakao, Y.; Kuo, J.; Yoshida, W. Y.; Kelly, M.; Scheuer, P. J. Org. Lett. 2003, 5, 1387
25. Takayama, H.; Mori, I.; Kitajima, M.; Aimi, N.; Lajis, N. H. Org. Lett. 2004, 6, 2945
26. Matsuda, Y.; Kitajima, M.; Takayama, H. Org. Lett. 2008, 10, 125
27. Newhouse, T.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 10886
28. Newhouse, T.; Lewis, C. A.; Eastman, K. J.; Baran, P. S. J. Am. Chem. Soc. 2010, 132, 7119
29. Takahashi, N.; Ito, T.; Matsuda, Y.; Kogure, N.; Kiyajima, M.; Takayama, H. Chem. Commun. 2010, 46, 2501
30. Foo, K.; Newhouse, T. R.; Mori, I.; Takayama, H.; Baran, P. S. Angew.Chem., Int. Ed. 2011, 50, 2716
31. Araki, T.; Ozawa, T.; Yokoe, H.; Kanematsu, M.; Yoshida, M.; Shishido, K. Org. Lett. 2013, 15, 200
32. Schallenberger, M. A.; Newhouse, T.; Baran, P. S.; Romesberg, F. E. J. Antibiot. 2010, 63, 685
33. Kung, A. L.; Zabludoff, S. D.; France, D. S.; Freedman, S. J.; Tanner, E. A.; Vieira, A.; Cornell-Kennon, S.; Lee, J.; Wang, B.; Wang, J.; Memmert, J.; Naegeli, H.-U.; Petersen, F.; Eck, M. J.; Bair, K. W.; Wood, A. W.; Livingston, D. M. Cancer Cell 2004, 6, 33
34. Masashi, H.; Mitsuyoshi, S.; Hiroshi, M.; Yuji, S. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1994, 36, 557
35. Li, G.-Y.; Li, B.-G.; Yang, T.; Yan, J.-F.; Liu, G.-Y.; Zhang, G.-L. J. Nat. Prod. 2006, 69, 1374
36. Ding, G.; Jiang, L.; Guo, L.; Chen, X.; Zhang, H.; Che, Y. J. Nat. Prod. 2008, 71, 1861
37. Emura, T.; Esaki, T.; Tachibana, K.; Shimizu, M. J. Org. Chem. 2006, 71, 8559
38. Bergonzini, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 971
39. Noole, A.; Järving, I.; Werner, F.; Lopp, M.; Malkov, A.; Kanger, T. Org. Lett. 2012, 14, 4922
40. Li, J.; Du, T.; Zhang, G.; Peng, Y. Chem. Commun. 2013, 49, 1330
41. Zhou, F.; Zeng, X.-P.; Wang, C.; Zhao, X.-L.; Zhou, J. Chem. Commun. 2013, 49, 2022
42. Hara, N.; Nakamura, S.; Sano, M.; Tamura, R.; Funahashi, Y.; Shibata, N. Chem.-Eur. J. 2012, 18, 9276
43. Chen, D.; Xu, M.-H. Chem. Commun. 2013, 49, 1327
44. Mouri, S.; Chen, Z.; Mitsunuma, H.; Furutachi, M.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255
45. Bui, T.; Hernández-Torres, G.; Milite, C.; Barbas, C. F., III. Org. Lett. 2010, 12, 5696
46. Ren, L.; Lian, X.-L.; Gong, L.-Z. Chem.-Eur. J. 2013, 19, 3315
47. Shen, K.; Liu, X.; Wang, G.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2011, 50, 4684
48. Espejo, V. R.; Rainier, J. D. J. Am. Chem. Soc. 2008, 130, 12894
49. Beaumont, S.; Pons, V.; Retailleau, P.; Dodd, R. H.; Dauban, P. Angew. Chem., Int. Ed. 2010, 49, 1634
50. Espejo, V. R.; Li, X.-B.; Rainier, J. D. J. Am. Chem. Soc. 2010, 132, 8282
51. Movassaghi, M.; Ahmad, O. K.; Lathrop, S. P. J. Am. Chem. Soc. 2011, 133, 13002
52. Benkovics, T.; Guzei, I. A.; Yoon, T. P. Angew. Chem., Int. Ed. 2010, 49, 9153
53. For a chiral phosphoric acid catalyzed example, see: Zhang, Z.; Antilla, J. C. Angew. Chem., Int. Ed. 2012, 51, 11778
54. For recent research which found that the electrophilic indol-2-one could be controlled by the chiral nickel(II) catalyst, see: Zhang, H.; Hong, L.; Kang, H.; Wang, R. J. Am. Chem. Soc. 2013, 135, 14098
55. Belmar, J.; Funk, R. L. J. Am. Chem. Soc. 2012, 134, 16941
56. Fuchs, J. R.; Funk, R. L. Org. Lett. 2005, 7, 677
57. Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068
58. Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 2431
59. Zuo, J.; Liao, Y.-H.; Zhang, X.; Yuan, W.-C. J. Org. Chem. 2012, 77, 11325
60. Liao, Y.-H.; Wu, Z.-J.; Han, W.-Y.; Zhang, X.-M.; Yuan, W.-C. Chem.-Eur. J. 2012, 18, 8916
61. Ma, S.; Han, X.; Krishnan, S.; Virgil, S. C.; Stoltz, B. M. Angew. Chem., Int. Ed. 2009, 48, 8037
62. Menozzi, C.; Dalko, P. I.; Cossy, J. Chem. Commun. 2006, 42, 4638
63. Xie, W.; Jiang, G.; Liu, H.; Hu, J.; Pan, X.; Zhang, H.; Wan, X.; Lai, Y.; Ma, D. Angew. Chem., Int. Ed. 2013, 52, 12924