Domino Pd-catalyzed heck cyclization and bismuth-catalyzed hydroamination: Formal synthesis of elacomine and isoelacomine

Chemistry - A European Journal

Volumn 17, Issue 2, 2011, Pages 626-633

  Kamisaki, Haruhi ^a   Nanjo, Takeshi ^a   Tsukano, Chihiro ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

bismuth; domino reactions; formal synthesis; palladium; spiro compounds

Indexed keywords

CARBAMOYL CHLORIDES; CARBON SKELETON; COUPLING PRODUCT; DOMINO REACTIONS; FORMAL SYNTHESIS; HECK CYCLIZATION; HECK REACTIONS; HYDROAMINATIONS; PYRROLIDINES; SPIRO COMPOUNDS;

AMIDES; BISMUTH; BISMUTH COMPOUNDS; CATALYSIS; CHLORINE COMPOUNDS; OLEFINS; PALLADIUM; REACTION INTERMEDIATES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

BISMUTH; ELACOMINE; INDOLE DERIVATIVE; ISOELACOMINE; PALLADIUM; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

BISMUTH; CATALYSIS; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; PALLADIUM; SPIRO COMPOUNDS;

EID: 78651256946     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002287     Document Type: Article

References (60)

1. G. W. A. Slywka, Ph.D. Thesis, The University of Alberta, Edmonton, 1969.
2. M. N. G. James, G. J. B. Williams, Can. J. Chem. 1972, 50, 2407.
3. C. Pellegrini, M. Eber, H.-J. Borschberg, Helv. Chim. Acta 1996, 79, 151.
4. For reviews, see C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209
5. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902
6. Angew. Chem. Int. Ed. 2007, 46, 8748
7. B. M. Trost, M. K. Brennan, Synthesis 2009, 3003; for recent synthetic studies of the related natural products, also see
8. J. E. M. N. Klein, A. Perry, D. S. Pugh, R. J. K. Taylor, Org. Lett. 2010, 12, 3446
9. V. J. Reddy, C. J. Douglas, Tetrahedron 2010, 66, 4719
10. J. E. Thomson, A. F. Kyle, K. B. Ling, S. R. Smith, A. M. Z. Slawin, A. D. Smith, Tetrahedron 2010, 66, 3801
11. V. J. Reddy, C. J. Douglas, Org. Lett. 2010, 12, 952
12. I. Allous, S. Comesse, D. BerkeÅ, A. Alkyat, A. Daãch, Tetrahedron Lett. 2009, 50, 4411
13. S. Jaegli, J.-P. Vors, L. Neuville, J. Zhu, Synlett 2009, 2997
14. J. Liang, J. Chen, F. Du, X. Zeng, L. Li, H. Zhang, Org. Lett. 2009, 11, 2820
15. J. Yang, X. Z. Wearing, P. W. L. Quesne, J. R. Deschamps, J. M. Cook, J. Nat. Prod. 2008, 71, 1431.
16. F. Y. Miyake, K. Yakushijin, D. A. Horne, Org. Lett. 2004, 6, 711.
17. J. D. White, Y. Li, D. C. Ihle, J. Org. Chem. 2010, 75, 3569.
18. H. Kamisaki, Y. Yasui, Y. Takemoto, Tetrahedron Lett. 2009, 50, 2589
19. Y. Yasui, H. Kamisaki, T. Ishida, Y. Takemoto, Tetrahedron 2010, 66, 1980.
20. L. E. Overman, M. D. Rosen, Angew. Chem. 2000, 112, 4768
21. Angew. Chem. Int. Ed. 2000, 39, 4596
22. L. E. Overman, M. D. Rosen, Tetrahedron 2010, 66, 6514.
23. S. Jaegli, W. Erb, P. Repailleau, J.-P. Vors, L. Neuville, J. Zhu, Chem. Eur. J. 2010, 16, 5863.
24. D. Lizos, R. Tripoli, J. A. Murphy, Chem. Commun. 2001, 2732.
25. D. M. D'Souza, A. Kiel, D.-P. Herten, F. Rominger, T. J. J. Müller, Chem. Eur. J. 2008, 14, 529.
26. R. T. Ruck, M. A. Huffman, M. M. Kim, M. Shevlin, W. V. Kandur, I. W. Davies, Angew. Chem. 2008, 120, 4789
27. Angew. Chem. Int. Ed. 2008, 47, 4711.
28. Y. Zhang, B. O'Connor, E. Negishi, J. Org. Chem. 1988, 53, 5588
29. J.-P. Genet, E. Blart, M. Savignac, Synlett 1992, 715
30. N. Garg, M. Larhed, A. Hallberg, J. Org. Chem. 1998, 63, 4158
31. D. Tanaka, A. G. Myers, Org. Lett. 2004, 6, 433
32. J. M. Ready, S. E. Reisman, M. Hirata, M. M. Weiss, K. Tamaki, T. V. Ovaska, J. L. Wood, Angew. Chem. 2004, 116, 1290
33. Angew. Chem. Int. Ed. 2004, 43, 1270
34. A. K. Gupta, C. H. Song, C. H. Oh, Tetrahedron Lett. 2004, 45, 4113
35. T. R. Krishna, N. Jayaraman, Tetrahedron 2004, 60, 10325
36. J.-H. Li, D.-P. Wang, Y.-X. Xie, Tetrahedron Lett. 2005, 46, 4941
37. J.-H. Li, D.-P. Wang, Y.-X. Xie, Synthesis 2005, 2193
38. M. K. Frömming, D. J. Sames, J. Am. Chem. Soc. 2007, 129, 14518
39. S. E. Reisman, J. M. Ready, M. M. Weiss, A. Hasuoka, M. Hirata, K. Tamaki, T. V. Ovaska, C. J. Smith, J. L. Wood, J. Am. Chem. Soc. 2008, 130, 2087
40. Y. Fall, H. Doucet, M. Santelli, Tetrahedron 2009, 65, 489.
41. For reviews of Mizoroki-Heck reaction, see W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2
42. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009
43. J. T. Link, in Organic Reactions, Vol 60, The Intramolecular Heck Reaction (Eds L. E. Overman et al), Wiley, Hoboken, New Jersey, 2002, pp. 157
44. A. Dounay, L. E. Overman, Chem. Rev. 2003, 103, 2945
45. A. Steven, L. E. Overman, Angew. Chem. 2007, 119, 5584
46. Angew. Chem. Int. Ed. 2007, 46, 5488.
47. During this study, one example of a Heck reaction with a six-membered unsaturated lactone was reported in a patent:, T. J. Commons, D. J. Jenkins, E. J. Trybulski, A. Fensome, US Pat. Appl. Publ. 2009, US 2009197878, A1 20090806.
48. B. P. Carrow, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 79.
49. N. Casamitjana, V. Lõpez, A. Jorge, J. Bosch, E. Molins, A. Roig, Tetrahedron 2000, 56, 4027.
50. Compound 10b was prepared by nosylation (oNsCl, nBuLi, THF, -78°C, 71%) of 5,6-dihydropyridine-2(1H)-one.
51. 3, see:, H. Gaspard-Iloughmane, C. L. Roux, Eur. J. Org. Chem. 2004, 2517.
52. The major diastereomer had the same stereochemistry of isoelacomine.
53. H. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 1611
54. H. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Chem. Asian J. 2007, 2, 150.
55. I. Fleming, Frontier Orbital and Organic Chemical Reactions, Wiley, London, 1976
56. T.-L. Ho, Hard and Soft Acids and Bases Principle in Organic Chemistry, Academic Press, New York, 1977
57. S. Woodward, Tetrahedron 2002, 58, 1017.
58. P. K. Freeman, L. L. Hutchinson, J. Org. Chem. 1980, 45, 1924
59. R. E. Ireland, M. G. Smith, J. Am. Chem. Soc. 1988, 110, 854
60. W. A. Carroll, P. A. Grieco, J. Am. Chem. Soc. 1993, 115, 1164.