Nucleophilic addition of grignard reagents to 3-acylindoles: Stereoselective synthesis of highly substituted indoline scaffolds

Organic Letters

Volumn 14, Issue 15, 2012, Pages 3978-3981

  Wang, Lu ^a   Shao, Yushang ^b   Liu, Yuanhong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INDOLE DERIVATIVE; INDOLINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

INDICATORS AND REAGENTS; INDOLES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84864582010     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301750b     Document Type: Article

References (46)

1. Indoles; Sundberg, R. J., Ed.; Academic Press: San Diego, 1996.
2. Indole Alkaloids; Rahman, A., Basha, A., Eds.; Harwood Academic: Amsterdam, 1998.
3. Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489
4. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
5. Sundberg, R. J. Top Heterocycl. Chem. 2010, 26, 47
6. Kishbaugh, T. L. S. Top Heterocycl. Chem. 2010, 26, 117
7. Gribble, G. W. Pure Appl. Chem. 2003, 75, 1417
8. Szmuszkovicz, J. J. Org. Chem. 1962, 27, 511
9. Pelkey, E. T.; Chang, L.; Gribble, G. W. Chem. Commun. 1996, 1909
10. Pelkey, E. T.; Gribble, G. W. Chem. Commun. 1997, 1873
11. Pelkey, E. T.; Gribble, G. W. Synthesis 1999, 1117
12. Pelkey, E. T.; Barden, T. C.; Gribble, G. W. Tetrahedron Lett. 1999, 40, 7615
13. Roy, S.; Gribble, G. W. Tetrahedron Lett. 2007, 48, 1003
14. Qian, D. C.; Alford, P. E.; Kishbaugh, T. L. S.; Jones, S. T.; Gribble, G. W. ARKIVOC 2010, iv) 66
15. Alford, P. E.; Kishbaugh, T. L. S.; Gribble, G. W. Heterocycles 2010, 80, 831
16. Somei, M.; Kawasaki, T.; Fukui, Y.; Yamada, F.; Kobayashi, T.; Aoyama, H.; Shinmyo, D. Heterocycles 1992, 34, 1877
17. Yamada, F.; Fukui, Y.; Shinmyo, D.; Somei, M. Heterocycles 1993, 35, 99
18. Somei, M. Heterocycles 1999, 50, 1157
19. Yamada, K.; Yamada, F.; Somei, M. Heterocycles 2002, 57, 1231
20. Yamada, K.; Yamada, F.; Shiraishi, T.; Tomioka, S.; Somei, M. Heterocycles 2009, 77, 971
21. Viswanathan, R.; Smith, C. R.; Prabhakaran, E. N.; Johnston, J. N. J. Org. Chem. 2008, 73, 3040
22. Hasegawa, K.; Kimura, N.; Arai, S.; Nishida, A. J. Org. Chem. 2008, 73, 6363
23. Liu, Y.; Xu, W.; Wang, X. Org. Lett. 2010, 12, 1448
24. Schammel, A. W.; Boal, B. W.; Zu, L.; Mesganaw, T.; Garg, N. K. Tetrahedron 2010, 66, 4687
25. Cera, G.; Crispino, P.; Monari, M.; Bandini, M. Chem. Commun. 2011, 47, 7803
26. Nguyen, Q.; Sun, K.; Driver, T. G. J. Am. Chem. Soc. 2012, 134, 7262
27. Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787
28. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893
29. Wang, L.; Li, G.; Liu, Y. Org. Lett. 2011, 13, 3786
30. Xie, X.; Du, X.; Chen, Y.; Liu, Y. J. Org. Chem. 2011, 76, 9175
31. Li, G.; Liu, Y. J. Org. Chem. 2010, 75, 3526
32. Li, H.; Yang, J.; Liu, Y.; Li, Y. J. Org. Chem. 2009, 74, 6797
33. Lu, Y.; Du, X.; Jia, X.; Liu, Y. Adv. Synth. Catal. 2009, 351, 1517
34. Li, G.; Wang, E.; Chen, H.; Li, H.; Liu, Y.; Wang, P. G. Tetrahedron 2008, 64, 9033
35. Boymond, L.; Rottländer, M.; Cahiez, G.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 1701
36. Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845
37. Teichert, J. F.; Feringa, B. L. Angew. Chem., Int. Ed. 2010, 49, 2486
38. Rathgeb, X.; March, S.; Alexakis, A. J. Org. Chem. 2006, 71, 5737
39. Howell, G. P.; Fletcher, S. P.; Geurts, K.; ter Horst, B.; Feringa, B. L. J. Am. Chem. Soc. 2006, 128, 14977
40. Gribble, G. W.; Saulnier, M. G. J. Org. Chem. 1983, 48, 607
41. Johnson, D. A.; Gribble, G. W. Heterocycles 1986, 24, 2127
42. Reference 5a, 5b.
43. Kolotaev, A. V.; Belen'kii, L. I.; Kononikhin, A. S.; Krayushkin, M. M. Russ. Chem. Bull. Int. Ed. 2006, 55, 892
44. Lee, S.; Park, S. B. Org. Lett. 2009, 11, 5214
45. Vecchione, M. K.; Sun, A. X.; Seidel, D. Chem. Sci. 2011, 2, 2178
46. Knepper, I.; Iaroshenko, V. O.; Vilches-Herrera, M.; Domke, L.; Mkrtchyan, S.; Zahid, M.; Villinger, A.; Langer, P. Tetrahedron 2011, 67, 5293