Palladium-catalyzed three-component tandem cyclization reaction of 2-(2,3-allenyl)acylacetates, organic halides, and amines: An effective protocol for the synthesis of 4,5-dihydro-1H-pyrrole derivatives

Advanced Synthesis and Catalysis

Volumn 353, Issue 10, 2011, Pages 1676-1682

  Cheng, Jiajia ^a   Jiang, Xuefeng ^a   Zhu, Can ^a   Ma, Shengming ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

4,5 dihydro 1H pyrroles; allenes; cyclization; three component reactions

Indexed keywords

EID: 79960464307     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100002     Document Type: Article

References (64)

1. For recent monographs and reviews on multi-component reactions: a)R. V. A. Orru, M. de Greef, Synthesis 2003, 1471
2. J. Zhu, Eur. J. Org. Chem. 2003, 1133
3. D. J. Ramõn, M. Yus, Angew. Chem. 2005, 117, 1628
4. Angew. Chem. Int. Ed. 2005, 44, 1602
5. Multicomponent Reactions, (Eds.:, J. Zhu, H. Bienaymé,), Wiley-VCH, Weinheim, 2005
6. A. Dömling, Chem. Rev. 2006, 106, 17
7. D. M. D'Souza, T. J. J. Müller, Chem. Soc. Rev. 2007, 36, 1095
8. Domino Reactions in Organic Synthesis, (Eds.:, L. F. Tietze, D. G. Brasche; K. M. Gericke,), Wiley-VCH, Weinheim, 2007
9. A. Alba, X. Companyo, M. Viciano, R. Rios, Curr. Org. Chem. 2009, 13, 1432
10. A. Basso, L. Banfi, R. Riva, Eur. J. Org. Chem. 2010, 1831.
11. For the most recent examples of multicomponent cycloadditions involving imine-enamine intermediates, see: a)J. Jiang, J. Yu, X.-X. Sun, Q.-Q. Rao, L.-Z. Gong, Angew. Chem. 2008, 120, 2492
12. Angew. Chem. Int. Ed. 2008, 47, 2458
13. B. O. Okandeji, J. R. Gordon, J. K. Sello, J. Org. Chem. 2008, 73, 5595
14. P. Jakubec, M. Helliwell, D. J. Dixon, Org. Lett. 2008, 10, 4267
15. W. Lu, W. Song, D. Hong, P. Lu, Y. Wang, Adv. Synth. Catal. 2009, 351, 1768
16. B.-L. Yang, Z.-T. Weng, S.-J. Yang, S.-K. Tian, Chem. Eur. J. 2010, 16, 718
17. H. Yang, R. G. Carter, Org. Lett. 2010, 12, 3108
18. L.-R. Wen, C. Liu, M. Li, L.-J. Wang, J. Org. Chem. 2010, 75, 7605.
19. For recent reviews on transition metal-catalyzed reactions for the synthesis heterocyclic compounds, see: a)G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285
20. I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127
21. P. R. Chopade, J. Louie, Adv. Synth. Catal. 2006, 348, 2307
22. V. Cadierno, P. Crochet, Curr. Org. Synth. 2008, 5, 343.
23. E. Baltazzi, L. I. Krimen, Chem. Rev. 1963, 63, 511
24. Heterocyclic Chemistry, 4 th edn., (Eds.:, J. A. Joule, K. Mills,), Blackwell, Oxford, 2000
25. B. A. Trofimov, L. N. Sobenina, A. P. Demenev, A. I. Mikhaleva, Chem. Rev. 2004, 104, 2481
26. H. Fan, J. Peng, M. T. Hamann, J.-F. Hu, Chem. Rev. 2008, 108, 264.
27. J. Davoll, J. Chem. Soc. 1953, 3802
28. R. J. S. Beer, W. T. Gradwell, W. J. Oates, J. Chem. Soc. 1958, 4693
29. A. Hassner, A. S. Miller, M. J. Haddadin, J. Org. Chem. 1972, 37, 2682
30. T. Eicher, J. L. Weber, Tetrahedron Lett. 1974, 15, 1381
31. C. Deshayes, S. Gelin, Synthesis 1981, 6, 466
32. S. Gelin, C. Deshayes, Synthesis 1982, 8, 657.
33. For reviews see: a)R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067
34. J. A. Marshall, Chem. Rev. 2000, 100, 3163
35. X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535
36. S. Ma, in: Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed:, Negishi, E.,), Wiley, New York, 2002, pp 1491-1523
37. R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12
38. S. Ma, Acc. Chem. Res. 2003, 36, 701
39. L.-L. Wei, H. Xiong, R. P. Hsung, Acc. Chem. Res. 2003, 36, 773
40. S. Ma, Chem. Rev. 2005, 105, 2829
41. S. Ma, in: Topics in Organometallic Chemistry, (Ed.:, J. Tsuji,), Springer-Verlag, Heidelberg, 2005, pp 183-210
42. S. Ma, Aldrichimica Acta 2007, 40, 91
43. M. Jeganmohan, C.-H. Cheng, Chem. Commun. 2008, 27, 3101
44. S. Ma, Acc. Chem. Res. 2009, 42, 1679
45. B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Soc. Rev. 2010, 39, 783.
46. For some of the recent reports from this group, see: a)S. Ma, Z. Zheng, X. Jiang, Org. Lett. 2007, 9, 529
47. X. Jiang, X. Ma, Z. Zheng, S. Ma, Chem. Eur. J. 2008, 14, 8572
48. X. Cheng, S. Ma, Angew. Chem. 2008, 120, 4657
49. Angew. Chem. Int. Ed. 2008, 47, 4581
50. X. Jiang, Q. Yang, Y. Yu, C. Fu, S. Ma, Chem. Eur. J. 2009, 15, 7283
51. X. Cheng, S. Ma, Chem. Commun. 2009, 28, 4263
52. W. Shu, Q. Yu, S. Ma, Adv. Synth. Catal. 2009, 351, 2807.
53. For some of the most recent reports on cyclization of allenes from other groups, see: a)S. Inuki, S. Oishi, N. Fujii, H. Ohno, Org. Lett. 2008, 10, 5239
54. B. M. Trost, J. Xie, J. Am. Chem. Soc. 2008, 130, 6231
55. H. Tsukamoto, T. Matsumoto, Y. Kondo, Org. Lett. 2008, 10, 1047
56. E. M. Beccalli, G. Broggini, F. Clerici, S. Galli, C. Kammerer, M. Rigamonti, S. Sottocornola, Org. Lett. 2009, 11, 1563
57. L. Rout, A. M. Harned, Chem. Eur. J. 2009, 15, 12926
58. M. Li, D. J. Dixon, Org. Lett. 2010, 12, 3784
59. M. Kalek, T. Johansson, M. Jezowska, J. Stawinski, Org. Lett. 2010, 12, 4702
60. M. P. Muñoz, M. C. de La Torre, Adv. Synth. Catal. 2010, 352, 2189
61. D. N. Tran, N. Cramer, Angew. Chem. 2010, 122, 8357
62. Angew. Chem. Int. Ed. 2010, 49, 8181
63. B. Alcaide, P. Almendros, R. Carrascosa, T. Martínez del Campo, Chem. Eur. J. 2010, 16, 13243
64. E. M. Beccalli, A. Bernasconi, E. Borsini, G. Broggini, M. Rigamonti, G. Zecchi, J. Org. Chem. 2010, 75, 6923.