Novel tartrate-derived guanidine-catalyzed highly enantio-and diastereoselective Michael addition of 3-substituted oxindoles to nitroolefins

Chemical Communications

Volumn 50, Issue 43, 2014, Pages 5760-5762

  Zou, Liwei ^a   Bao, Xiaoze ^a   Ma, Yuanyuan ^a   Song, Yuming ^a   Qu, Jingping ^a   Wang, Baomin ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; GUANIDINE; OXINDOLE; TARTARIC ACID; ALKENE; INDOLE DERIVATIVE; NITRO DERIVATIVE; TARTARIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; REACTION TIME; ROOM TEMPERATURE; STEREOCHEMISTRY; STEREOISOMERISM; CHEMISTRY; ENZYME SPECIFICITY;

ALKENES; CATALYSIS; GUANIDINE; INDOLES; NITRO COMPOUNDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TARTRATES;

EID: 84899831611     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc01817f     Document Type: Article

References (57)

1. C. Marti, E. M. Carreira, Eur. J. Org. Chem., 2003, 2209
2. A. B. Dounay, L. E. Overman, Chem. Rev., 2003, 103, 2945
3. C. V. Galliford, K. A. Scheidt, Angew. Chem., Int. Ed., 2007, 46, 8748
4. F. Zhou, Y.-L. Liu, J. Zhou, Adv. Synth. Catal., 2010, 352, 1381
5. J. E. M. N. Klein, R. J. K. Taylor, Eur. J. Org. Chem., 2011, 6821
6. G. S. Singh, Z. Y. Desta, Chem. Rev., 2012, 112, 6104
7. K. Shen, X. Liu, L. Lin, X. Feng, Chem. Sci., 2012, 3, 327
8. R. Dalpozzo, G. Bartoli, G. Bencivenni, Chem. Soc. Rev., 2012, 41, 7247
9. A. Perry, R. J. K. Taylor, Chem. Commun., 2009, 3249
10. J. E. M. N. Klein, A. Perry, D. S. Pugh, R. J. K. Taylor, Org. Lett., 2010, 12, 3446
11. W. Fu, F. Xu, Y. Fu, M. Zhu, J. Yu, C. Xu, D. Zou, J. Org. Chem., 2013, 78, 12202
12. S.-L. Zhou, L.-N. Guo, H. Wang, X.-H. Duan, Chem. – Eur. J., 2013, 19, 12970
13. G. Luppi, P. G. Cozzi, M. Monari, B. Kaptein, Q. B. Broxterman, C. Tomasini, J. Org. Chem., 2005, 70, 7418
14. L. Liu, S. Zhang, F. Xue, G. Lou, H. Zhang, S. Ma, W. Duan, W. Wang, Chem. – Eur. J., 2011, 17, 7791
15. Q. Ren, J. Huang, L. Wang, W. Li, H. Liu, X. Jiang, J. Wang, ACS Catal., 2012, 2, 2622
16. I. Saidalimu, X. Fang, X.-P. He, J. Liang, X. Yang, F. Wu, Angew. Chem., Int. Ed., 2013, 52, 5566
17. B. Zhu, W. Zhang, R. Lee, Z. Han, W. Yang, D. Tan, K.-W. Huang, Z. Jiang, Angew. Chem., Int. Ed., 2013, 52, 6666
18. D. Monge, A. M. Crespo-Peña, E. Martín-Zamora, E. Álvarez, R. Fernández, J. M. Lassaletta, Chem. – Eur. J., 2013, 19, 8421
19. Z. Duan, J. Han, P. Qian, Z. Zhang, Y. Wang, Y. Pan, Org. Biomol. Chem., 2013, 11, 6456
20. A. Kumar, S. S. Chimni, Tetrahedron, 2013, 69, 5197
21. F. Pesciaioli, P. Righi, A. Mazzanti, G. Bartoli, G. Bencivenni, Chem. – Eur. J., 2011, 17, 2842
22. C. Curti, G. Rassu, V. Zambrano, L. Pinna, G. Pelosi, A. Sartori, L. Battistini, F. Zanardi, G. Casiraghi, Angew. Chem., Int. Ed., 2012, 51, 6200
23. T. Ishimaru, N. Shibata, J. Nagai, S. Nakamura, T. Toru, S. Kanemasa, J. Am. Chem. Soc., 2006, 128, 16488
24. D. Sano, K. Nagata, T. Itoh, Org. Lett., 2008, 10, 1593
25. T. Bui, N. R. Candeias, C. F. Barbas III, J. Am. Chem. Soc., 2010, 132, 5574
26. Z. Zhang, W. Zheng, J. C. Antilla, Angew. Chem., Int. Ed., 2011, 50, 1135
27. Y. Yang, F. Moinodeen, W. Chin, T. Ma, Z. Jiang, C.-H. Tan, Org. Lett., 2012, 14, 4762
28. T. Zhang, L. Cheng, S. Hameed, L. Liu, D. Wang, Y.-J. Chen, Chem. Commun., 2011, 47, 6644
29. L. Li, W. Chen, W. Yang, Y. Pan, H. Liu, C.-H. Tan, Z. Jiang, Chem. Commun., 2012, 48, 5124
30. Y.-H. Liao, X.-L. Liu, Z.-J. Wu, X.-L. Du, X.-M. Zhang, W.-C. Yuan, Chem. – Eur. J., 2012, 18, 6679
31. F. Zhong, X. Dou, X. Han, W. Yao, Q. Zhu, Y. Meng, Y. Lu, Angew. Chem., Int. Ed., 2013, 52, 943
32. T. Bui, S. Syed, C. F. Barbas III, J. Am. Chem. Soc., 2009, 131, 8758
33. R. He, S. Shirakawa, K. Maruoka, J. Am. Chem. Soc., 2009, 131, 16620
34. X. Li, B. Zhang, Z.-G. Xi, S. Luo, J.-P. Cheng, Adv. Synth. Catal., 2010, 352, 416
35. M. Ding, F. Zhou, Z.-Q. Qian, J. Zhou, Org. Biomol. Chem., 2010, 8, 2912
36. M. Ding, F. Zhou, Y.-L. Liu, C.-H. Wang, X.-L. Zhao, J. Zhou, Chem. Sci., 2011, 2, 2035
37. X.-L. Liu, Z.-J. Wu, X.-L. Du, X.-M. Zhang, W.-C. Yuan, J. Org. Chem., 2011, 76, 4008
38. X. Li, Y.-M. Li, F.-Z. Peng, S.-T. Wu, Z.-Q. Li, Z.-W. Sun, H.-B. Zhang, Z.-H. Shao, Org. Lett., 2011, 13, 6160
39. Y.-M. Li, X. Li, F.-Z. Peng, Z.-Q. Li, S.-T. Wu, Z.-W. Sun, H.-B. Zhang, Z.-H. Shao, Org. Lett., 2011, 13, 6200
40. C. Wang, X. Yang, D. Enders, Chem. – Eur. J., 2012, 18, 4832
41. K. Albertshofer, B. Tan, C. F. Barbas III, Org. Lett., 2012, 14, 1834
42. W. Yang, J. Wang, D.-M. Du, Tetrahedron: Asymmetry, 2012, 23, 972
43. B.-D. Cui, W.-Y. Han, Z.-J. Wu, X.-M. Zhang, W.-C. Yuan, J. Org. Chem., 2013, 78, 8833
44. X. Dou, B. Zhou, W. Yao, F. Zhong, C. Jiang, Y. Lu, Org. Lett., 2013, 15, 4920
45. Y. Kato, M. Furutachi, Z. Chen, H. Mitsunuma, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc., 2009, 131, 9168
46. Y.-Y. Han, Z.-J. Wu, W.-B. Chen, X.-L. Du, X.-M. Zhang, W.-C. Yuan, Org. Lett., 2011, 13, 5064
47. O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem., 2002, 1877
48. T. Ishikawa, T. Kumamoto, Synthesis, 2006, 737
49. D. Leow, C.-H. Tan, Chem. – Asian J., 2009, 4, 488
50. M. P. Coles, Chem. Commun., 2009, 3659
51. Y. Sohtome, K. Nagasawa, Synlett, 2010, 1
52. D. Leow, C.-H. Tan, Synlett, 2010, 1589
53. T. Ishikawa, Chem. Pharm. Bull., 2010, 58, 1555
54. P. Selig, Synthesis, 2013, 703
55. L. Zou, B. Wang, H. Mu, H. Zhang, Y. Song, J. Qu, Org. Lett., 2013, 15, 3106
56. W. Ye, D. Leow, S. L. M. Goh, C.-T. Tan, C.-H. Chian, C.-H. Tan, Tetrahedron Lett., 2006, 47, 1007
57. Z. Yu, X. Liu, L. Zhou, L. Lin, X. Feng, Angew. Chem., Int. Ed., 2009, 48, 5195