N-heterocyclic carbene-catalyzed homoenolate additions with N-Aryl ketimines as electrophiles: Efficient synthesis of spirocyclic γ-lactam oxindoles

Chemistry - A European Journal

Volumn 18, Issue 30, 2012, Pages 9198-9203

  Zhang, Bo ^a   Feng, Peng ^a   Sun, Li Hui ^c   Cui, Yuxin ^a   Ye, Song ^c   Jiao, Ning ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c INSTITUTE OF CHEMISTRY   (China)

Author keywords

carbenes; lactams; organocatalysis; spiro compounds; umpolung

Indexed keywords

CARBENES; LACTAMS; ORGANOCATALYSIS; SPIRO COMPOUNDS; UMPOLUNG;

ALDEHYDES; AMIDES; CATALYSIS; REACTION KINETICS;

ORGANIC COMPOUNDS;

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; IMINE; INDOLE DERIVATIVE; KETIMINE; LACTAM; METHANE; NITRILE; OXINDOLE; SPIRO COMPOUND;

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

CATALYSIS; HETEROCYCLIC COMPOUNDS; IMINES; INDOLES; LACTAMS; METHANE; MOLECULAR STRUCTURE; NITRILES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84863966354     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201375     Document Type: Article

References (86)

1. The Chemistry of Heterocyclic Compounds, Vol. 25 (Eds.:, E. C. Taylor, J. E. Saxton,), Wiley-Interscience, New York, 1994
2. R. J. Sundberg, Indoles, Academic, New York, 1996
3. T. Kawasaki, K. Higuchi, Nat. Prod. Rep. 2005, 22, 761
4. N. Saracoglu, Top. Heterocycl. Chem. 2007, 11, 145-178.
5. C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209
6. B. M. Trost, C. Jiang, Synthesis 2006, 369
7. B. M. Trost, M. K. Brennan, Synthesis 2009, 3003
8. R. M. Williams, R. J. Cox, Acc. Chem. Res. 2003, 36, 127
9. H. Lin, S. J. Danishefsky, Angew. Chem. 2003, 115, 38
10. Angew. Chem. Int. Ed. 2003, 42, 36
11. C. V. Galliford, K. A. Scheidt, Angew. Chem. 2007, 119, 8902
12. Angew. Chem. Int. Ed. 2007, 46, 8748
13. F. Zhou, Y.-L. Liu, J. Zhou, Adv. Synth. Catal. 2010, 352, 1381.
14. R. R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, J. Med. Chem. 2008, 51, 5731
15. M. J. Kornet, A. P. Thio, J. Med. Chem. 1976, 19, 892
16. N. Arumugam, G. Periyasami, R. Raghunathan, S. Kamalraj, J. Muthumary, Eur. J. Med. Chem. 2011, 46, 600
17. R. S. Kumar, S. M. Rajesh, S. Perumal, D. Banerjee, P. Yogeeswari, D. Sriram, Eur. J. Med. Chem. 2010, 45, 411
18. A. S. Girgis, Eur. J. Med. Chem. 2009, 44, 1257
19. M. A. Ali, R. Ismail, T. S. Choon, Y. K. Yoon, A. C. Wei, S. Pandian, R. S. Kumar, H. Osman, E. Manogaran, Bioorg. Med. Chem. Lett. 2010, 20, 7064.
20. N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. 2007, 119, 3046
21. Angew. Chem. Int. Ed. 2007, 46, 2988
22. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606
23. V. Nair, S. Vellalath, B. P. Babu, Chem. Soc. Rev. 2008, 37, 2691
24. J. L. Moore, T. Rovis, Top. Curr. Chem. 2009, 291, 77
25. A. T. Bigu, N. Kuhl, F. Glorius, Acc. Chem. Res. 2011, 44, 1182
26. V. Nair, R. S. Menon, A. T. Biju, C. R. Sinu, R. R. Paul, A. Jose, V. Sreekumar, Chem. Soc. Rev. 2011, 40, 5336.
27. D. Seebach, Angew. Chem. 1979, 91, 259
28. Angew. Chem. Int. Ed. Engl. 1979, 18, 239.
29. R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719
30. H. Stetter, M. Schreckenberg, Angew. Chem. 1973, 85, 89
31. Angew. Chem. Int. Ed. Engl. 1973, 12, 81.
32. L. Baragwanath, C. A. Rose, K. Zeitler, S. J. Connon, J. Org. Chem. 2009, 74, 9214
33. N. Kuhl, F. Glorius, Chem. Commun. 2011, 47, 573
34. C. A. Rose, S. Gundala, C.-L. Fagan, J. F. Franz, S. J. Connon, K. Zeitler, Chem. Sci. 2012, 3, 735
35. E. Sánchez-Larios, K. Thai, F. Bilodeau, M. Gravel, Org. Lett. 2011, 13, 4942
36. J. M. Um, D. A. DiRocco, E. L. Noey, T. Rovis, K. N. Houk, J. Am. Chem. Soc. 2011, 133, 11249
37. D. A. DiRocco, T. Rovis, J. Am. Chem. Soc. 2011, 133, 10402.
38. C. Burstein, F. Glorius, Angew. Chem. 2004, 116, 6331
39. Angew. Chem. Int. Ed. 2004, 43, 6205.
40. S. S. Sohn, E. L. Rosen, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 14370.
41. S. S. Sohn, E. L. Rosen, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 14370
42. K. Hirano, I. Piel, F. Glorius, Adv. Synth. Catal. 2008, 350, 984
43. C. Burstein, F. Glorius, Angew. Chem. 2004, 116, 6331
44. Angew. Chem. Int. Ed. 2004, 43, 6205
45. S. S. Sohn, J. W. Bode, Org. Lett. 2005, 7, 3873
46. J. Kaeobamrung, M. C. Kozlowski, J. W. Bode, Proc. Natl. Acad. Sci. USA 2010, 107, 20661
47. V. Nair, S. Vellalath, M. Poonoth, R. Mohan, E. Suresh, Org. Lett. 2006, 8, 507
48. L.-H. Sun, L.-T. Shen, S. Ye, Chem. Commun. 2011, 47, 10136.
49. M. He, J. W. Bode, J. Am. Chem. Soc. 2008, 130, 418
50. A. Chan, K. A. Scheidt, Org. Lett. 2005, 7, 905
51. M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 8418
52. M. Wadamoto, E. M. Phillips, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 10098
53. A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2008, 130, 2740
54. Y. Li, X.-Q. Wang, C. Zhang, S.-L. You, Chem. Commun. 2009, 5823
55. Z. Chen, X. Yu, J. Wu, Chem. Commun. 2010, 46, 6356
56. J. Ma, Y. Huang, R. Chen, Org. Biomol. Chem. 2011, 9, 1791
57. X. Fang, K. Jiang, C. Xing, L. Hao, Y. R. Chi, Angew. Chem. 2011, 123, 1950
58. Angew. Chem. Int. Ed. 2011, 50, 1910
59. P.-C. Chiang, J. Kaeobamrung, J. W. Bode, J. Am. Chem. Soc. 2007, 129, 3520
60. V. Nair, S. Vellalath, M. Poonoth, E. Suresh, J. Am. Chem. Soc. 2006, 128, 8736
61. V. Nair, C. R. Sinu, B. P. Babu, V. Varghese, A. Jose, E. Suresh, Org. Lett. 2009, 11, 5570
62. J. Seayad, P. K. Patra, Y. Zhang, J. Y. Ying, Org. Lett. 2008, 10, 953
63. E. M. Phillips, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2008, 130, 2416
64. A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 5334
65. M. Rommel, T. Fukuzumi, J. W. Bode, J. Am. Chem. Soc. 2008, 130, 17266.
66. M. Rommel, T. Fukuzumi, J. W. Bode, J. Am. Chem. Soc. 2008, 130, 17266
67. M. He, J. W. Bode, Org. Lett. 2005, 7, 3131.
68. A. Chan, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 5334.
69. E. M. Phillips, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2008, 130, 2416.
70. X. Zhao, D. A. DiRocco, T. Rovis, J. Am. Chem. Soc. 2011, 133, 12466.
71. Z. Shi, C. Zhang, S. Li, D. Pan, S. Ding, Y. Cui, N. Jiao, Angew. Chem. 2009, 121, 4642
72. Angew. Chem. Int. Ed. 2009, 48, 4572
73. Z. Shi, S. Ding, Y. Cui, N. Jiao, Angew. Chem. 2009, 121, 8035
74. Angew. Chem. Int. Ed. 2009, 48, 7895
75. Z. Shi, B. Zhang, Y. Cui, N. Jiao, Angew. Chem. 2010, 122, 4130
76. Angew. Chem. Int. Ed. 2010, 49, 4036
77. Z. Shi, Y. Cui, N. Jiao, Org. Lett. 2010, 12, 2908
78. S. Ding, Z. Shi, Y. Cui, N. Jiao, Org. Lett. 2010, 12, 1540
79. S.-K. Xiang, B. Zhang, L.-H. Zhang, Y. Cui, N. Jiao, Chem. Commun. 2011, 47, 8097
80. R. Lin, S. Ding, Z. Shi, N. Jiao, Org. Lett. 2011, 13, 4498
81. S. Ding, N. Jiao, J. Am. Chem. Soc. 2011, 133, 12374.
82. B. Alcaide, P. Almendros, C. Aragoncillo, Eur. J. Org. Chem. 2010, 2845
83. Y.-L. Liu, F. Zhou, J.-J. Cao, C.-B. Ji, M. Ding, J. Zhou, Chem. Commun. 2010, 8, 3847.
84. H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796.
85. J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798.
86. C. J. Collins, M. Lanz, B. Singaram, Tetrahedron Lett. 1999, 40, 3673.