Organocatalytic asymmetric vinylogous Michael addition of dicyanoolefins to imine intermediates generated in situ from arenesulfonylalkylindoles

Advanced Synthesis and Catalysis

Volumn 354, Issue 16, 2012, Pages 2965-2970

  Zhu, Xing Li ^a   He, Wu Jun ^a   Yu, Liang Liang ^a   Cai, Chang Wu ^a   Zuo, Zong Le ^a   Qin, Da Bin ^a   Liu, Quan Zhong ^a   Jing, Lin Hai ^a  

^a CHINA WEST NORMAL UNIVERSITY   (China)

Author keywords

arenesulfonylalkylindoles; asymmetric catalysis; dicyanoolefins; organic catalysis; vinylogous Michael addition

Indexed keywords

EID: 84869028817     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200286     Document Type: Article

References (103)

1. R. J. Sundberg, Indoles, Academic Press, London, 1996
2. J. E. Saxton, Nat. Prod. Rep. 1997, 14, 559-590
3. D. J. Faulkner, Nat. Prod. Rep. 2002, 19, 1-48
4. E. M. K. Wijeratne, T. J. Turbyville, Z. Zhang, D. Bigelow, L. S. Pierson, H. D. VanEtten, L. Whitesell, L. M. Canfield, A. A. L. Gunatilaka, J. Nat. Prod. 2003, 66, 1567-1573
5. Y. Feng, J. W. Blunt, A. L. J. Cole, M. H. G. Munro, J. Nat. Prod. 2004, 67, 2090-2092
6. Y. Usami, J. Yamaguchi, A. Numata, Heterocycles 2004, 63, 1123-1129
7. J.-Y. Dong, H.-P. He, Y.-M. Shen, K.-Q. Zhang, J. Nat. Prod. 2005, 68, 1510-1513
8. C.-J. Zheng, C.-J. Kim, K. S. Bae, Y.-H. Kim, W.-G. Kim, J. Nat. Prod. 2006, 69, 1816-1819
9. G. Carr, W. Tay, H. Bottriell, S. K. Andersen, A. G. Mauk, R. J. Andersen, Org. Lett. 2009, 11, 2996-2999.
10. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786-9824
11. Angew. Chem. Int. Ed. 2009, 48, 9608-9644
12. G. Bartoli, G. Bencivenni, R. Dalpozzo, Chem. Soc. Rev. 2010, 39, 4449-4465
13. M. Shiri, Chem. Rev. 2012, 112, 3508-3549.
14. M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566
15. Angew. Chem. Int. Ed. 2004, 43, 550-556
16. M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett 2005, 1199-1222
17. T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903-2915
18. E. Marques-Lopez, A. Diez-Martinez, P. Merino, R. P. Herrera, Curr. Org. Chem. 2009, 13, 1585-1609
19. S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190-2201
20. M. Zeng, S.-L. You, Synlett 2010, 1289-1301.
21. R. Ballini, A. Palmieri, M. Petrini, E. Torregiani, Org. Lett. 2006, 8, 4093-4096.
22. A. Palmieri, M. Petrini, R. R. Shaikh, Org. Biomol. Chem. 2010, 8, 1259-1270
23. F. Martinelli, A. Palmieri, M. Petrini, Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 1032-1045.
24. A. Palmieri, M. Petrini, J. Org. Chem. 2007, 72, 1863-1866
25. A. Palmieri, M. Petrini, E. Torregiani, Tetrahedron Lett. 2007, 48, 5653-5656
26. R. Ballini, A. Palmieri, M. Petrini, R. R. Shaikh, Adv. Synth. Catal. 2008, 350, 129-134
27. A. Palmieri, M. Petrini, R. R. Shaikh, Synlett 2008, 1845-1851
28. M. Petrini, R. R. Shaikh, Tetrahedron Lett. 2008, 49, 5645-5648
29. M. Petrini, R. R. Shaikh, Synthesis 2009, 3143-3149
30. R. Ballini, S. Gabrielli, A. Palmieri, M. Petrini, Adv. Synth. Catal. 2010, 352, 2459-2462
31. R. Dubey, B. Olenyuk, Tetrahedron Lett. 2010, 51, 609-612
32. L. Marsili, A. Palmieri, M. Petrini, Org. Biomol. Chem. 2010, 8, 706-712.
33. R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8835-8838
34. Angew. Chem. Int. Ed. 2008, 47, 8707-8710
35. Y. Li, F.-Q. Shi, Q.-L. He, S.-L. You, Org. Lett. 2009, 11, 3182-3185
36. M. C. Dobish, J. N. Johnston, Org. Lett. 2010, 12, 5744-5747
37. L. Jing, J. Wei, L. Zhou, Z. Huang, Z. Li, D. Wu, H. Xiang, X. Zhou, Chem. Eur. J. 2010, 16, 10955-10958
38. B.-H. Zheng, C.-H. Ding, X.-L. Hou, L.-X. Dai, Org. Lett. 2010, 12, 1688-1691
39. L.-L. Cao, Z.-S. Ye, G.-F. Jiang, Y.-G. Zhou, Adv. Synth. Catal. 2011, 353, 3352-3356
40. J. Wang, S. Zhou, D. Lin, X. Ding, H. Jiang, H. Liu, Chem. Commun. 2011, 47, 8355-8357
41. M. Fochi, L. Gramigna, A. Mazzanti, S. Duce, S. Fantini, A. Palmieri, M. Petrini, L. Bernardi, Adv. Synth. Catal. 2012, 354, 1373-1380.
42. G. Casiraghi, F. Zanardi, G. Appendino, G. Rassu, Chem. Rev. 2000, 100, 1929-1972
43. S. K. Bur, S. F. Martin, Tetrahedron 2001, 57, 3221-3242
44. S. F. Martin, Acc. Chem. Res. 2002, 35, 895-904
45. A. Soriente, R. M. De, R. Villano, A. Scettri, Curr. Org. Chem. 2004, 8, 993-1007
46. S. E. Denmark, J. R. Heemstra, G. L. Beutner, Angew. Chem. 2005, 117, 4760-4777
47. Angew. Chem. Int. Ed. 2005, 44, 4682-4698
48. S. Hosokawa, K. Tatsuta, Mini-Rev. Org. Chem. 2008, 5, 1-18
49. T. Brodmann, M. Lorenz, R. Schäckel, S. Simsek, M. Kalesse, Synlett 2009, 174-192
50. G. Casiraghi, F. Zanardi, L. Battistini, G. Rassu, Synlett 2009, 1525-1542
51. G. Casiraghi, L. Battistini, C. Curti, G. Rassu, F. Zanardi, Chem. Rev. 2011, 111, 3076-3154.
52. For a review on α,α-dicyanoolefins as vinylogous nucleophiles, see:, H.-L. Cui, Y.-C. Chen, Chem. Commun. 2009, 4479-4486.
53. T. B. Poulsen, C. Alemparte, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 11614-11615
54. T. B. Poulsen, M. Bell, K. A. Jørgensen, Org. Biomol. Chem. 2006, 4, 63-70
55. B. Niess, K. A. Jørgensen, Chem. Commun. 2007, 1620-1622
56. J. Aleman, C. B. Jacobsen, K. Frisch, J. Overgaard, K. A. Jørgensen, Chem. Commun. 2008, 632-634.
57. D. Xue, Y.-C. Chen, Q.-W. Wang, L.-F. Cun, J. Zhu, J.-G. Deng, Org. Lett. 2005, 7, 5293-5296
58. J.-W. Xie, L. Yue, D. Xue, X.-L. Ma, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Chem. Commun. 2006, 1563-1565
59. L. Jiang, H.-T. Zheng, T.-Y. Liu, L. Yue, Y.-C. Chen, Tetrahedron 2007, 63, 5123-5128
60. T.-Y. Liu, H.-L. Cui, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, J. Am. Chem. Soc. 2007, 129, 1878-1879
61. J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393-396
62. Angew. Chem. Int. Ed. 2007, 46, 389-392
63. T.-R. Kang, J.-W. Xie, W. Du, X. Feng, Y.-C. Chen, Org. Biomol. Chem. 2008, 6, 2673-2675
64. H.-L. Cui, J. Peng, X. Feng, W. Du, K. Jiang, Y.-C. Chen, Chem. Eur. J. 2009, 15, 1574-1577
65. X.-F. Xiong, Z.-J. Jia, W. Du, K. Jiang, T.-Y. Liu, Y.-C. Chen, Chem. Commun. 2009, 6994-6996
66. J. Peng, X. Huang, H.-L. Cui, Y.-C. Chen, Org. Lett. 2010, 12, 4260-4263.
67. J. Lu, F. Liu, T.-P. Loh, Adv. Synth. Catal. 2008, 350, 1781-1784
68. J. Lu, F. Liu, W.-J. Zhou, T.-P. Loh, Tetrahedron Lett. 2008, 49, 5389-5392
69. J. Lu, W.-J. Zhou, F. Liu, T.-P. Loh, Adv. Synth. Catal. 2008, 350, 1796-1800.
70. Q.-A. Chen, W. Zeng, D.-W. Wang, Y.-G. Zhou, Synlett 2009, 2236-2241
71. Q.-A. Chen, D.-S. Wang, Y.-G. Zhou, Chem. Commun. 2010, 46, 4043-4051.
72. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286
73. Angew. Chem. Int. Ed. 2004, 43, 5138-5175
74. A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005
75. Y. Hayashi, J. Synth. Org. Chem. Jpn. 2005, 63, 464-477
76. J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724
77. B. List; J. W. Yang, Science 2006, 313, 1584-1586
78. B. List, Chem. Commun. 2006, 819-824
79. Enantioselective Organocatalysis, (Ed.:, P. I.Dalko,), Wiley-VCH, Weinheim, 2007
80. H. Pellissier, Tetrahedron 2007, 63, 9267-9331
81. M. J. Gaunt, C. C. C. Johansson, A. McNally, N. T. Vo, Drug Discovery Today 2007, 12, 8-27
82. S. Jaroch, H. Weinmann, K. Zeitler, ChemMedChem 2007, 2, 1261-1264
83. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743
84. A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716-4739
85. Angew. Chem. Int. Ed. 2008, 47, 4638-4660
86. D. W. C. MacMillan, Nature 2008, 455, 304-308
87. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232-6265
88. Angew. Chem. Int. Ed. 2008, 47, 6138-6171
89. C. F. Barbas, Angew. Chem. 2008, 120, 44-50
90. Angew. Chem. Int. Ed. 2008, 47, 42-47
91. J. T. Mohr, M. R. Krout, B. M. Stoltz, Nature 2008, 455, 323-332
92. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178-2189
93. A.-N. Alba, X. Companyo, M. Viciano, R. Rios, Curr. Org. Chem. 2009, 13, 1432-1474
94. special issues: Adv. Synth. Catal. 2004, 346, 1007-1249
95. Acc. Chem. Res. 2004, 37, 487-631
96. Tetrahedron 2006, 62, 243-502
97. Chem. Rev. 2007, 107, 5413-5883.
98. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673
99. T. Okino, S. Nakamura, T. Furukawa, Y. Takemoto, Org. Lett. 2004, 6, 625-627
100. T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119-125. For a more recent review, see
101. Y. Takemoto, Chem. Pharm. Bull. 2010, 58, 593-601.
102. A. A. Fadda, H. M. Refat, Synth. Commun. 2000, 30, 341-350.
103. CCDC 873716 (4a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.