Highly diastereo- and enantioselective michael additions of 3-substituted oxindoles to maleimides catalyzed by chiral bifunctional thiourea-tertiary amine

Organic Letters

Volumn 12, Issue 13, 2010, Pages 2896-2899

  Liao, Yu Hua ^a,b   Liu, Xiong Li ^a,b   Wu, Zhi Jun ^b,c   Cun, Lin Feng ^a   Zhang, Xiao Mei ^a   Yuan, Wei Cheng ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; INDOLE DERIVATIVE; MALEIMIDE DERIVATIVE; OXINDOLE; THIOUREA;

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

AMINES; CATALYSIS; INDOLES; MALEIMIDES; MOLECULAR STRUCTURE; STEREOISOMERISM; THIOUREA;

EID: 77954111282     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100822k     Document Type: Article

References (80)

1. For reviews of related stereoselective construction of contiguous quaternary-tertiary carbon centers, see: Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688
2. Ramon, D. J.; Yus, M. Curr. Org. Chem. 2004, 8, 149
3. Peterson, E. A.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11943
4. Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473
5. Trost, B. M.; Jiang, C. Synthesis 2006, 369
6. Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969
7. For selected examples of related stereoselective construction of vicinal quaternary-tertiary carbon centers, see: Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 11204
8. Austin, J. F.; Kim, S.-G.; Sinz, C. J.; Xiao, W.-J.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482
9. Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105
10. Poulsen, T. B.; Alemparte, C.; Saaby, S.; Bella, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 2896
11. Lalonde, M. P.; Chen, Y.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 6366
12. van Steenis, D. J. V. C.; Marcelli, T.; Lutz, M.; Spek, A. L.; van Maarseveen, J. H.; Hiemstra, H. Adv. Synth. Catal. 2007, 349, 281
13. For selected reviews, see: Hibino, S.; Choshi, T. Nat. Prod. Rep. 2001, 18, 66
14. Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36
15. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945
16. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
17. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
18. For selected examples, see
19. Wearing, X. Z.; Cook, J. M. Org. Lett. 2002, 4, 4237
20. Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197
21. Huang, A.; Kodanko, J. J.; Overman, L. E. J. Am. Chem. Soc. 2004, 126, 14043
22. Abadi, A. H.; Abou-Seri, S. M.; Abdel-Rahman, D. E.; Klein, C.; Lozach, O.; Meijer, L. Eur. J. Med. Chem. 2006, 41, 296
23. Reisman, S. E.; Ready, J. M.; Weiss, M. M.; Hasuoka, A.; Hirata, M.; Tamaki, K.; Ovaska, T. V.; Smith, C. J.; Wood, J. L. J. Am. Chem. Soc. 2008, 130, 2087
24. Ruck, R. T.; Huffman, M. A.; Kim, M. M.; Shevlin, M.; Kandur, W. V.; Davies, I. W. Angew. Chem., Int. Ed. 2008, 47, 4711
25. For transition-metal-catalyzed asymmetric reactions, see: Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M. J. Am. Chem. Soc. 2005, 127, 10164
26. Trost, B. M.; Brennan, M. K. Org. Lett. 2006, 8, 2027
27. Toullec, P. Y.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2006, 8, 2715
28. Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353
29. Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488
30. Jia, Y.-X.; Hillgren, J. M.; Watson, E. L.; Marsden, S. P.; Kündig, E. P. Chem. Commun. 2008, 4040
31. Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 6946
32. Hanhan, N. V.; Sahin, A. H.; Chang, W.; Fettinger, J. C.; Franz, A. K. Angew. Chem., Int. Ed. 2010, 49, 744
33. For organocatalytic asymmetric reactions, see: Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921
34. Luppi, G.; Cozzi, P. G.; Monari, M.; Kaptein, B.; Broxterman, Q. B.; Tomasini, C. J. Org. Chem. 2005, 70, 7418
35. Bella, M.; Kobbelgaard, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 3670
36. Shaw, S. A.; Aleman, P.; Christy, J.; Kampf, J. W.; Va, P.; Vedejs, E. J. Am. Chem. Soc. 2006, 128, 925
37. Ogawa, S.; Shibata, N.; Inagaki, J.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2007, 46, 8666
38. Nakamura, S.; Hara, N.; Nakashima, H.; Kubo, K.; Shibata, N.; Toru, T. Chem.-Eur. J. 2008, 14, 8079
39. Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157
40. Tian, X.; Jiang, K.; Peng, J.; Du, W.; Chen, Y.-C. Org. Lett. 2008, 10, 3583
41. Sano, D.; Nagata, K.; Itoh, T. Org. Lett. 2008, 10, 1593
42. Duffey, T. A.; Shaw, S. A.; Vedejs, E. J. Am. Chem. Soc. 2009, 131, 14
43. Jiang, K.; Peng, J.; Cui, H.-L.; Chen, Y.-C. Chem. Commun. 2009, 3955
44. Cheng, L.; Liu, L.; Jia, H.; Wang, D.; Chen, Y.-J. Org. Lett. 2009, 11, 3874
45. Qian, Z.-Q.; Zhou, F.; Du, T.-P.; Wang, B.-L.; Ding, M.; Zhao, X.-L.; Zhou, J. Chem. Commun. 2009, 6753
46. Cheng, L.; Liu, L.; Jia, H.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2009, 74, 4650
47. Galzerano, P.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem.-Eur. J. 2009, 15, 7846
48. He, R.; Ding, C.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48, 4559
49. Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819
50. Li, X.; Xi, Z.-G.; Luo, S.; Cheng, J.-P. Org. Biomol. Chem. 2010, 8, 77
51. Li, X.; Zhang, B.; Xi, Z.-G.; Luo, S. Z.; Cheng, J.-P. Adv. Synth. Catal. 2010, 352, 416
52. For recently selected examples of maleimides used in organic synthesis, see: Hilt, G.; Lüers, S.; Smolko, K. I. Org. Lett. 2005, 7, 251
53. Cabrera, S.; Arrayás, R. G.; Carretero, J. C. J. Am. Chem. Soc. 2005, 127, 16394
54. Shen, J.; Nguyen, T. T.; Goh, Y.-P.; Ye, W.; Fu, X.; Xu, J.; Tan, C.-H. J. Am. Chem. Soc. 2006, 128, 13692
55. Zu, L.; Xie, H.; Li, H.; Wang, J.; Jiang, W.; Wang, W. Adv. Synth. Catal. 2007, 349, 1882
56. Ye, W.; Jiang, Z.; Zhao, Y.; Goh, S. L. M.; Leow, D.; Soh, Y.-T.; Tan, C.-H. Adv. Synth. Catal. 2007, 349, 2454
57. Nájera, C.; Retamosa, M. G.; Sansano, J. M. Org. Lett. 2007, 9, 4025
58. Lu, J.; Zhou, W.-J.; Liu, F.; Loh, T.-P. Adv. Synth. Catal. 2008, 350, 1796
59. Soh, J. Y.-T.; Tan, C.-H. J. Am. Chem. Soc. 2009, 131, 6904
60. For a recent review of organocatalytic formation of quaternary stereocenters, see
61. Marco, B.; Tecla, G. Synthesis 2009, 1583 and references cited therein
62. For selected reviews of bifunctional urea and thiourea catalysts, see: Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299
63. Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520
64. Connon, S. J. Chem.-Eur. J. 2006, 12, 5418
65. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
66. Miyabe, H.; Takemoto, Y. Bull. Chem. Soc. Jpn. 2008, 81, 785
67. Connon, S. J. Synlett 2009, 354
68. Zheng, H.-J.; Chen, W.-B.; Wu, Z.-J.; Deng, J.-G.; Lin, W.-Q.; Yuan, W.-C.; Zhang, X.-M. Chem.-Eur. J. 2008, 14, 9864
69. Liao, Y.-H.; Zhang, H.; Wu, Z.-J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron: Asymmetry 2009, 20, 2397
70. Xue, Z.-Y.; Jiang, Y.; Yuan, W.-C.; Zhang, X.-M. Eur. J. Org. Chem. 2010, 616
71. Chen, W.-B.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2010, 66, 1441
72. Liao, Y.-H.; Chen, W.-B.; Wu, Z.-J.; Du, L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Adv. Synth. Catal 2010, 352, 827
73. Zhang, H.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Lett. Org. Chem. 2010, 7, 219
74. Ballini, R.; Bosica, G.; Fiorini, D.; Palmeiri, A.; Petrini, M. Chem. Rev. 2005, 105, 933
75. Shibasaki, M.; Matsunaga, S. Chem, Soc, Rev. 2006, 35, 269
76. Ting, A.; Schaus, S. E. Eur, J. Org. Chem. 2007, 5797
77. For selected examples using catalysts that closely resemble 1d, see: Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2007, 127, 119
78. Li, B.-J.; Lin, J.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Synlett 2005, 603
79. Liu, T.-Y.; Long, J.; Li, B.-J.; Jiang, L.; Li, R.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Org. Biomol. Chem. 2006, 4, 2097
80. Marini, F.; Sternativo, S.; Del Verme, F.; Testaferri, L.; Tiecco, M. Adv. Synth. Catal. 2009, 351, 103