Isocyanide-based multicomponent reactions: Catalyst-free stereoselective construction of polycyclic spiroindolines

Organic Letters

Volumn 15, Issue 8, 2013, Pages 1954-1957

  Wang, Xiang ^a   Wang, Shun Yi ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; INDOLE DERIVATIVE; NITRILE;

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

CATALYSIS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDOLES; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM;

EID: 84876593078     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400606c     Document Type: Article

References (56)

1. Tietze, L. F. Chem. Rev. 1996, 96, 115-136
2. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
3. Rosamilia, A. E.; Strauss, C. R.; Scott, J. L. Pure Appl. Chem. 2007, 79, 1869-1877
4. Chen, C.; Li, X.; Neumann, C. S.; Lo, M. M. C.; Schreiber, S. L. Angew. Chem., Int. Ed. 2005, 44, 2249-2252
5. Mitchell, J. M.; Shaw, J. T. Angew. Chem., Int. Ed. 2006, 45, 1722-1726
6. Kumagai, N.; Muncipinto, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2006, 45, 3635-3638
7. Thomas, G. L.; Spandl, R. J.; Glansdorp, F. G.; Welch, M.; Bender, A.; Cockfield, J.; Lindsay, J. A.; Bryant, C.; Brown, D. F. J.; Loiseleur, O.; Rudyk, H.; Ladlow, M.; Spring, D. R. Angew. Chem., Int. Ed. 2008, 47, 2808-2812
8. Domling, A. Chem. Rev. 2006, 106, 17-89
9. Zhu, J.; Bienayme, H., Eds. Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005.
10. Toure, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439-4486
11. Ganem, B. Acc. Chem. Res. 2009, 42, 463-472
12. Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, V.; Zografos, S. L. J. Am. Chem. Soc. 2009, 131, 1753-1765
13. Muller, F. L.; Constantieux, T.; Rodriguez, J. J. Am. Chem. Soc. 2005, 127, 17176-17177
14. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186
15. Diguez-Vzquez, A.; Tzschucke, C. C.; Lam, W. Y.; Ley, S. V. Angew. Chem., Int. Ed. 2008, 47, 209-212
16. Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210
17. Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602-1634
18. Santra, S.; Andreana, P. R. Angew. Chem., Int. Ed. 2011, 50, 9418-9422
19. Enders, D.; Huttl, M. R. M.; Grondal, C.; Raab, G. Nature 2006, 441, 861-863
20. Andrey, S. I. Chem. Soc. Rev. 2008, 37, 789-811
21. de Meijere, A.; von Zezschwitz, P.; Brase, S. Acc. Chem. Res. 2005, 38, 413-422
22. Huang, Y.; Waljji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051-15053
23. Yang, J. W.; Fonseca, H. M. T.; List, B. J. Am. Chem. Soc. 2005, 127, 15036-15037
24. Barluenga, J.; Jimenez-Aquino, A.; Valdes, C.; Aznar, F. Angew. Chem., Int. Ed. 2007, 46, 15292-15293
25. Alex, K.; Tillack, A.; Schwarz, N.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 2304-2307
26. Lu, M.; Zhu, D.; Lu, Y.; Hou, B.; Tan, B.; Zhong, G. Angew. Chem., Int. Ed. 2008, 47, 10187-10191
27. Wang, J.; Xie, H.; Li, H.; Zu, L.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177-4179
28. Bonjoch, J.; Sole, D. Chem. Rev. 2000, 100, 3455-3482
29. Sirasani, G.; Paul, T.; Dougherty, W.; Kassel, S.; Andrade, R. B. J. Org. Chem. 2010, 75, 3529-3532
30. Martin, D. B. C.; Vanderwal, C. D. Chem. Sci. 2011, 2, 649-651
31. Jones, S. B.; Simmons, B.; Mastracchio, A.; MacMillan, D.W. C. Nature 2011, 475, 183-188
32. Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007, 129, 13794-13795
33. Zuo, Z.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2010, 132, 13226-13228
34. Zuo, Z.; Ma, D. Isr. J. Chem. 2011, 51, 434-441
35. Zhang, D.; Song, H.; Qin, Y. Acc. Chem. Res. 2011, 44, 447-457
36. Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem., Int. Ed. 2010, 49, 2000-2003
37. Zuo, Z.; Ma, D. Angew. Chem., Int. Ed. 2011, 50, 12008-12011
38. Siengalewicz, P.; Gaich, T.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 8170-8176
39. Sundberg, R. J. Indoles; Academic Press: London, 1996.
40. Gribble, G. W. Heterocyclic Scaffolds II: Reactions and Applications of Indoles; Springer-Verlag: Berlin, Heidelberg, 2010; Vol. 26.
41. Saxton, J. E. Indoles, Part 4: The Monoterpenoid Indole Alkaloids; Wiley: Chichester, U.K., 1983.
42. Herbert, R. B. In The Monoterpenoid Indole Alkaloids; supplement to Vol. 25, part 4, of The Chemistry of Heterocyclic Compounds; Saxton, J. E., Ed.; Wiley: Chichester, U.K., 1994; Chapter 1.
43. Saxton, J. E. The Monoterpenoid Indole Alkaloids; supplement to Vol. 25, part 4, of The Chemistry of Heterocyclic Compounds; Saxton, J. E., Ed.; Wiley: Chichester, U.K., 1994; Chapter 8.
44. Saxton, J. E. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50.
45. Saxton, J. E. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 51, Chapter 1.
46. Toyota, M.; Ihara, M. Nat. Prod. Rep. 1998, 327
47. Janot, M.-M.; Pourrat, H.; Le Men, J. Bull. Soc. Chim. Fr. 1954, 707-708
48. Wenkert, E. J. Am. Chem. Soc. 1962, 84, 98-102
49. Modha, S. G.; Kumar, A.; Vachhani, D. D.; Jacobs, J.; Sharma, S. K.; Parmar, V. S.; Van Meervelt, L.; Van der Eycken, E. V. Angew. Chem., Int. Ed. 2012, 57, 9572-9575
50. Kaim, L. E.; Grimaud, L.; Goff, X. L.; Menes-Arzate, M.; Miranda, L. D. Chem. Commun. 2011, 47, 8145-8147
51. Fan, F.; Xie, W.; Ma, D. Org. Lett. 2012, 14, 1405-1407
52. Zheng, D.; Li, S.; Luo, Y.; Wu, J. Org. Lett. 2011, 13, 6402-6405
53. Zheng, D.; Li, S.; Wu, J. Org. Lett. 2012, 14, 2655-2657
54. Liu, H.; Domling, A. J. Org. Chem. 2009, 74, 6895-6898
55. Wang, W.; Herdtweck, E.; Domling, A. Chem. Commun. 2010, 46, 770-772
56. Mironov, M. A.; Ivantsova, M. N.; Mokrushin, V. S. Synlett 2006, 4, 615-618