Synthesis of spiro[chroman/tetrahydrothiophene-3,3'-oxindole] scaffolds via heteroatom-michael-michael reactions: Easily controlled enantioselectivity via bifunctional catalysts

Advanced Synthesis and Catalysis

Volumn 356, Issue 2-3, 2014, Pages 579-583

  Huang, Youming ^a   Zheng, Changwu ^a   Chai, Zhuo ^a   Zhao, Gang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric catalysis; Cascade reactions; Heteroatom Michael Michael reaction; Organocatalysis; Spirooxindoles

Indexed keywords

EID: 84899897142     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300833     Document Type: Article

References (65)

1. K. Kumar, H. Waldmann, Angew. Chem. 2009, 121, 3272
2. Angew. Chem. Int. Ed. 2009, 48, 3224
3. K. A. Miller, S. Tsukamoto, R. M. Williams, Nat. Chem. 2009, 1, 63
4. J. W. H. Li, J. C. Vederas, Science 2009, 325, 161
5. T. J. Greshock, A.W. Grubbs, P. Jiao, D. T. Wicklow, J. B. Gloer, R. M. Williams, Angew. Chem. 2008, 120, 3629
6. Angew. Chem. Int. Ed. 2008, 47, 3573
7. D. J. Newman, G. M. Cragg, J. Nat. Prod. 2007, 70, 461
8. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902
9. Angew. Chem. Int. Ed. 2007, 46, 8748.
10. L. Hong, R. Wang Adv. Synth. Catal. 2013, 355, 1
11. R. Dalpozzo, G. Bartoli, G. Bencivenni, Chem. Soc. Rev. 2012, 41, 7247
12. G. S. Singh, Z. Y. Desta, Chem. Rev. 2012, 112, 6104
13. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902
14. Angew. Chem. Int. Ed. 2007, 46, 8748.
15. X. Tian P. Melchiorre, Angew. Chem. Int. Ed. 2013, 52, 5360
16. L.-T. Shen, W.-Q. Jia, S. Ye Angew. Chem. 2013, 125, 613
17. Angew. Chem. Int. Ed. 2013, 52, 585
18. K. S. Halskov, T. K. Johansen, R. L. Davis, M. Steurer, F. Jensen, K. A. Jørgensen, J. Am. Chem. Soc. 2012, 134, 12943
19. A. Noole, N. S. Sucman, M. A. Kabeshov, T. Kanger, F. Z. Macaev, A. V. Malkov, Chem. Eur. J. 2012, 18, 14929
20. X. Dou, Y.-X. Lu, Chem. Eur. J. 2012, 18, 8315
21. F. Pesciaioli, P. Righi, A. Mazzanti, G. Bartoli, G. Bencivenni, Chem. Eur. J. 2011, 17, 2842
22. B. Tan, R. N. Candeias, C. F. Barbas III, J. Am. Chem. Soc. 2011, 133, 4672
23. B. Tan, R. N. Candeias, C. F. Barbas III, Nat. Chem. 2011, 3, 473
24. F. Zhong, X. Han, Y. Wang, Y.-X. Lu, Angew. Chem. 2011, 123, 7983
25. Angew. Chem. Int. Ed. 2011, 50, 7837
26. S. Duce, F. Pesciaioli, L. Gramigna, L. Bernardi, A. Mazzanti, A. Ricci, G. Bartoli, G. Bencivenni, Adv. Synth. Catal. 2011, 353, 860
27. C. Lu, Q. Xiao, P. E. Floreancig, Org. Lett. 2010, 12, 5112
28. B. Westermann, M. Ayaz, S. S. van Berkel, Angew. Chem. 2010, 122, 858
29. Angew. Chem. Int. Ed. 2010, 49, 846
30. X.-H. Chen, Q. Wei, S.-W. Luo, H. Xiao, L.-Z. Gong, J. Am. Chem. Soc. 2009, 131, 13819.
31. Y.-Y. Han, W.-B. Chen, W.-Y. Han, Z.-J. Wu, X.-M. Zhang, W.-C. Yuan, Org. Lett. 2012, 14, 490
32. S.-L. Zhu, S.-J. Ji, Z. Yong, Tetrahedron 2007, 63, 9365
33. A. H. Abdel-Rahman, E. M. Keshk, M. A. Hanna, S. M. El-Bady, Bioorg. Med. Chem. 2004, 12, 2483
34. J. F. M. Da-Silva, S. J. Garden, A. C. Pinto, J. Braz. Chem. Soc. 2001, 12, 273.
35. H. Pellissier, Adv. Synth. Catal. 2012, 354, 237
36. D. Enders, C. Grondal, R. M. H. Matthias, Angew. Chem. 2007, 119, 1590
37. Angew. Chem. Int. Ed. 2007, 46, 1570
38. J.-C. Wasilke, J. S. Obrey, R. T. Baker, C. B. Guillermo, Chem. Rev. 2005, 105, 1001.
39. G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaoli, M.-P. Song, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7336
40. Angew. Chem. Int. Ed. 2009, 48, 7200
41. D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006, 441, 861
42. N. Halland, P. S. Aburel, K. A. Jorgensen, Angew. Chem. 2004, 116, 1292
43. Angew. Chem. Int. Ed. 2004, 43, 1272
44. K. A. Ahrendt, C. J. Borths, D. W. C. Macmillan, J. Am. Chem. Soc. 2000, 122, 4243.
45. S. B. Jones, B. Simmons, D. W. C. Macmillan, J. Am. Chem. Soc. 2009, 131, 13606
46. Y. Hoashi, T. Yabuta, Y. Takemoto, Tetrahedron Lett. 2004, 45, 9185.
47. Y.-M. Huang, C.-W. Zheng, G. Zhao, RSC Adv. 2013, 3, 16999
48. W. Yang, D. Du, Chem. Commun. 2013, 49, 8842.
49. H.-B. Mao, A.-j. Lin, Y. Tang, Y. Shi, H.-W. Hu, Y.-X. Cheng, C.-J. Zhu, Org. Lett. 2013, 15, 4062.
50. K. C. Nicolaou, J. A. Pfefferkorn, A. J. Roecker, G.-Q. Cao, S. Barluenga, H. J. Mitchell, J. Am. Chem. Soc. 2000, 122, 9939, and references cited therein
51. B. A. Keay, in: Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Eds. Scriven), Pergamon, Oxford, 1996, Vol. 2, p 395
52. S. G. Das, J. M. Doshi, D. F. Tian, S. N. Addo, B. Srinivasan, D. L. Hermanson, C.-G. Xing, J. Med. Chem. 2009, 52, 5937
53. F. Shaheen, M. Ahmad, S. N. Khan, S. S. Hussain, S. Anjum, B. Tashkhodjaev, K. Turgunov, M. N. Sultankhodzhaev, M. I. Choudhary, A. Rahman, Eur. J. Org. Chem. 2006, 10, 2371.
54. R. Eskandari, K. Jayakanthan, D. A. Kuntz, D. R. Rose, B. M. Pinto, Bioorg. Med. Chem. 2010, 18, 2829
55. D. A. Kuntz, A. Ghavami, B. D. Johnston, B. M. Pinto, D. R. Rose, Tetrahedron: Asymmetry 2005, 16, 25
56. J. Wirsching, J. Voss, G. Adiwidjaja, J. Balzarini, E. De Clercq, Bioorg. Med. Chem. Lett. 2001, 11, 1049.
57. Z. Chai, G. Zhao, Catal. Sci. Technol. 2012, 2, 29
58. H. Xiao, Z. Chai, H.-F. Wang, X.-W. Wang, D.-D. Cao, W. Liu, Y.-P. Lu, Y.-Q. Yang, G. Zhao, Chem. Eur. J. 2011, 17, 10562
59. H.-F. Wang, P. Li, H.-F. Cui, X.-W. Wang, J.-K. Zhang, W. Liu, G. Zhao, Tetrahedron 2011, 67, 1774
60. X.-Y. Han, F.-R. Zhong, Y.-Q. Wang, Y.-X. Lu, Synlett 2011, 19, 2766
61. H. Xiao, Z. Chai, C.-W. Zheng, Y.-Q. Yang, W. Liu, J.-K. Zhang, G. Zhao, Angew. Chem. 2010, 122, 4569
62. Angew. Chem. Int. Ed. 2010, 49, 4467
63. P. Li, Z. Chai, S.-L. Zhao, Y.-Q. Yang, H.-F. Wang, C.-W. Zheng, Y.-P. Cai, G. Zhao, S.-Z. Zhu, Chem. Commun. 2009, 45, 7369
64. Y.-Q. Yang, G. Zhao, Chem. Eur. J. 2008, 14, 10888.
65. F. Yu, H.-X. Hu, X.-D. Gu, J.-X. Ye, Org. Lett. 2012, 14, 2038.