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http://dx.doi.org/10.5012/bkcs.2010.31.5.1280

Asymmetric Michael Addition of Ketones to Nitroolefins Catalyzed by a New Chiral Catalyst  

Wang, Lian-Jun (College of Chemistry and Chemical Engineering, Hunan Institute of Engineering)
Hu, Feng-Feng (College of Chemistry and Chemical Engineering, Hunan Institute of Engineering)
Publication Information
Abstract
A new chiral catalyst was synthesized and found that it could catalyzed the asymmetric Michael reaction of ketones with nitroolefins smoothly at room temperature, giving the desired adducts in 71 - 92% yields with excellent diastereoselectivities and high enantioselectivities (up to 95% ee).
Keywords
Chiral catalyst; Michael reaction; Nitroolefin; Ketone; Enantioselectivity;
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1 Hayashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem., Int. Ed. 2005, 44, 4032.   DOI   ScienceOn
2 Tsogoeva, S. B.; Wei, S. Chem. Commun. 2006, 1451.
3 Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.   DOI   ScienceOn
4 Hoashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem. Int. Ed. 2005, 44, 4032.   DOI   ScienceOn
5 Tsogoeva, S. B.; Wei, S. W. Chem. Commun. 2006, 1451.
6 Cao, C. L.; Ye, M. C.; Sun, X. L.; Tang, Y. Org. Lett. 2006, 8, 2904.
7 Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700.   DOI   ScienceOn
8 Brandau, S.; Landa, A.; Franzen, J.; Marigo, M.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 4305.   DOI   ScienceOn
9 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.   DOI   ScienceOn
10 Wang, Y.; Liu, X. F.; Deng, L. J. Am. Chem. Soc. 2006, 128, 1928.
11 Huang, H. B.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170.   DOI   ScienceOn
12 Diner, P.; Nielsen, M.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983.   DOI   ScienceOn
13 Tang, B.; Zeng, X. F.; Lu, Y. P.; Chua, P. J.; Zhong, G. F. Org. Lett. 2009, 11, 1927.   DOI   ScienceOn
14 Lo, C. M.; Chow, H. F. J. Org. Chem. 2009, 74, 5181.   DOI   ScienceOn
15 Wang, J.; Li, H.; Lou, B.; Zu, L. S.; Guo, H.; Wang, W. Chem. Eur. J. 2006, 12, 4321.   DOI   ScienceOn
16 Tan, B.; Zeng, X. F.; Lu, Y. P; Chua, P. J.; Zhong, G. F. Org. Lett. 2009, 11, 1927.   DOI   ScienceOn
17 Zeng, X. F.; Zhong, G. F. Synthesis 2009, 1545.
18 Shah, J.; Khah, S. S.; Blumenthal, H.; Liebscher, J. Synthesis 2009, 3975.
19 Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.   DOI   ScienceOn
20 Okino, T.; Hoashi, Y.; Furukawa, T.; Wu, X. N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.   DOI   ScienceOn
21 Cao, C. L.; Sun, X. L.; Zhou, J. L.; Tang, Y. J. Org. Chem. 2007, 72, 4073.   DOI   ScienceOn
22 Cao, C. L.; Ye, M. C.; Sun, X. L.; Tang, Y. Org. Lett. 2006, 8, 2901.   DOI   ScienceOn
23 Jiang, X. X.; Zhang, Y. F.; Chan, A. S. C.; Wang, R. Org. Lett. 2009, 11, 153.   DOI   ScienceOn
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.   DOI   ScienceOn
26 Mandal, T.; Zhao, C. G. Angew. Chem., Int. Ed. 2008, 47, 7714.   DOI   ScienceOn
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.   DOI   ScienceOn
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.   DOI   ScienceOn
31 Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X. N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.   DOI   ScienceOn
32 Kumaran, G.; Kulkarni, G. H. Synthesis 1995, 1545.
33 Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
34 Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192.   DOI   ScienceOn