Asymmetric Michael addition of ketones to nitroolefins catalyzed by a new chiral catalyst

Bulletin of the Korean Chemical Society

Volumn 31, Issue 5, 2010, Pages 1280-1282

  Wang, Lian Jun ^a   Hu, Feng Feng ^a  

^a HUNAN INSTITUTE OF ENGINEERING   (China)

Author keywords

Chiral catalyst; Enantioselectivity; Ketone; Michael reaction; Nitroolefin

Indexed keywords

CHIRAL CATALYST; DIASTEREOSELECTIVITIES; HIGH ENANTIOSELECTIVITY; MICHAEL ADDITIONS; MICHAEL REACTIONS; NITROOLEFINS; ROOM TEMPERATURE;

ADDITION REACTIONS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; KETONES; SYNTHESIS (CHEMICAL);

CATALYSTS;

EID: 77952666618     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.5.1280     Document Type: Article

References (34)

1. Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
2. For example: (a) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192.
3. Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700.
4. Some papers after 2006: (a) Brandau, S.; Landa, A.; Franzen, J.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 4305.
5. Bartoli, G.; Bosco, M.; Carlone, A.; Cavalli, A.; Locatelli, M.; Mazzanti, A.; Ricci, P.; Sambri, L.; Melchiorre, P. Angew. Chem., Int. Ed. 2006, 45, 4966.
6. Wang, Y.; Liu, X. F.; Deng, L. J. Am. Chem. Soc. 2006, 128, 1928.
7. Huang, H. B.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170.
8. Diner, P.; Nielsen, M.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983.
9. Tang, B.; Zeng, X. F.; Lu, Y. P.; Chua, P. J.; Zhong, G. F. Org. Lett. 2009, 11, 1927.
10. Lo, C. M.; Chow, H. F. J. Org. Chem. 2009, 74, 5181.
11. Zeng, X. F.; Zhong, G. F. Synthesis 2009, 1545.
12. Shah, J.; Khah, S. S.; Blumenthal, H.; Liebscher, J. Synthesis 2009, 3975.
13. For example: (a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
14. Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X. N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
15. Hayashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem., Int. Ed. 2005, 44, 4032.
16. Tsogoeva, S. B.; Wei, S. Chem. Commun. 2006, 1451.
17. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.
18. For example: (a) Hoashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem. Int. Ed. 2005, 44, 4032.
19. Tsogoeva, S. B.; Wei, S. W. Chem. Commun. 2006, 1451.
20. Okino, T.; Hoashi, Y.; Furukawa, T.; Wu, X. N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
21. Cao, C. L.; Sun, X. L.; Zhou, J. L.; Tang, Y. J. Org. Chem. 2007, 72, 4073.
22. Cao, C. L.; Ye, M. C.; Sun, X. L.; Tang, Y. Org. Lett. 2006, 8, 2901.
23. Jiang, X. X.; Zhang, Y. F.; Chan, A. S. C.; Wang, R. Org. Lett. 2009, 11, 153.
24. Cao, Y. J.; Lu, H. H.; Lai, Y. Y.; Lu, L. Q.; Xiao, W. J. Synthesis 2006, 3795.
25. Cheng, D. P.; Bao, W. L. Lett. Org. Chem. 2008, 5, 342.
26. Mandal, T.; Zhao, C. G. Angew. Chem., Int. Ed. 2008, 47, 7714.
27. Lu, A. D.; Gao, P.; Wu, Y.; Wang, Y. M.; Zhou, Z. H.; Tang, C. C. Org. Biomol. Chem. 2009, 7, 3141.
28. Dahlin, N.; Boegevig, A.; Adolfsson, H. Adv. Synth. Catal. 2004, 346, 1101.
29. Kando, Y.; Uneme, H.; Minamida, I. Eur. Pat. Appl. 1991 EP 452782.
30. Wakita, T.; Kinoshita, K.; Yasui, N.; Yamada, E.; Kawahara, N.; Kodaka, K. J. Pestic. Sci. 2004, 29, 348.
31. Kumaran, G.; Kulkarni, G. H. Synthesis 1995, 1545.
32. Wang, J.; Li, H.; Lou, B.; Zu, L. S.; Guo, H.; Wang, W. Chem. Eur. J. 2006, 12, 4321.
33. Tan, B.; Zeng, X. F.; Lu, Y. P; Chua, P. J.; Zhong, G. F. Org. Lett. 2009, 11, 1927.
34. Cao, C. L.; Ye, M. C.; Sun, X. L.; Tang, Y. Org. Lett. 2006, 8, 2904.