Asymmetric Epoxidation of Olefins Catalyzed by Chiral Ketones

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (4): 380-385. Previous Articles Next Articles

手性酮催化的烯烃不对称环氧化反应

王春^*,a, 吴秋华^b, 杨丽华^a, 唐然肖^a, 杨旭哲^a,果秀敏^a, 冯硕^a,b, 李贵深^a

^a河北农业大学理学院保定 071001
^b河北农业大学生物无机重点实验室保定 071001

收稿日期:2003-04-25 修回日期:2003-08-26 接受日期:2003-09-04 发布日期:2022-09-19

Asymmetric Epoxidation of Olefins Catalyzed by Chiral Ketones

WANG, Chun^*,a, WU, Qiu-Hua^b, YANG, Li-Hua^a, TANG, Ran-Xiao^a, YANG, Xu-Zhe^a, GUO, Xiu-Min^a, FENG, Shuo^a,b, LI, Gui-Shen^a

^aCollege of Science, Agricultural University of Hebei, Baoding 071001
^bKey Laboratory of Bioinorganic Chemistry, Agricultural University of Hebei, Baoding 071001

Received:2003-04-25 Revised:2003-08-26 Accepted:2003-09-04 Published:2022-09-19
Contact: *E-mail: wangc69@yahoo.com.cn

Abstract

Chiral ketone is a powerful catalyst for asymmetric epoxidation of unfunctionalized olefins. Dioxiranes, which could be generated in situ from chiral ketone and potassium peroxomonosulfate (Oxone), are remarkably effective oxidation reagents for asymmetric epoxidation of olefins. The application of a variety of chiral ketones in enantioselective epoxidation of trans-olefins, trisubstituted olefins and cis-olefins isreviewed. The catalytic activity and the asymmetric induction influenced by thestructure of chiral ketone and the reaction conditions are also discussed.

Key words: chiral ketone, asymmetric epoxidation, unfunctionalized olefin, dioxifane

Cite this article

WANG, Chun, WU, Qiu-Hua, YANG, Li-Hua, TANG, Ran-Xiao, YANG, Xu-Zhe, GUO, Xiu-Min, FENG, Shuo, LI, Gui-Shen. Asymmetric Epoxidation of Olefins Catalyzed by Chiral Ketones[J]. Chinese Journal of Organic Chemistry, 2004, 24(4): 380-385.

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References

1 Lin, G.-Q.; Chen, Y.-Q.; Chen, X.-Z.; Li, Y.-M.Chiral Synthesis-Asymmetric Reaction and Its Appication, Science Press, Beijing, 2000, p. 159 (in Chinese).
(林国强, 陈耀全, 陈新滋, 李月明, 手性合成不对称反应及其应用, 科学出版社, 北京, 2000, p. 159.)
2 Bonini, C.; Righi, G. Synthesis 1994, 225.
3 Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 2000,122, 4831.
4 Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
5 Zhang, W.; Leobach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801.
6 Irie, R.; Noda, K.; Ito, Y.; Katsuki, K. Tetrahedron Lett.1990, 31, 7345.
7 Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628.
8 Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155.
9 Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659.
10 Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3521.
11 Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491.
12 Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J.Am. Chem. Soc. 1996, 118, 11311.
13 Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
14 Denmark, S.-E.; Wu, Z. Synlett 1999, 847.
15 Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
16 Wang, Z. X.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62(8), 2328.
17 Wang, Z. X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
18 Cao, G.-A.; Wang, Z.-X.; Tu, Y.; Shi, Y. Tetrahedron Lett. 1998, 39, 4425.
19 Zhu, Y.-M.; Tu, Y.; Yu, H.-W.; Shi, Y. Tetrahedron Lett. 1998, 39, 7819.
20 Wang, Z.-X.; Cao, G.-A.; Shi, Y. J. Org. Chem. 1999,64, 7646.
21 Tu, Y.; Wang, Z.-X.; Frohn, M.; He, M.; Yu, H.; Tang, Y.; Shi, Y.J. Org. Chem. 1998, 63, 8475.
22 Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
23 Shu, L.-H.; Wang, P.-Z.; Gan, Y.-H.; Shi, Y. Org. Lett. 2003, 5, 293.
24 Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551.
25 Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435.
26 Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929.
27 Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622.
28 Wang, Z.-X.; Miller, S.-M.; Anderson, O.-P.; Shi, Y. J. Org. Chem. 1999, 64, 6443.
29 Wang, Z.-X.; Miller, S.-M.; Anderson, O.-P.; Shi, Y. J. Org. Chem. 2001, 66, 521.
30 Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621.
31 Armstrong, A.; Hayter, B.-R.; Moss, W.-O.; Reeves, J.-R.; Wailes, J.-S. Tetrahedron: Asymmetry 2000, 11, 2057.
32 Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288.
33 Denmark, S. E.; Wu, Z. Synlett 1999, 847.

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手性酮催化的烯烃不对称环氧化反应

Asymmetric Epoxidation of Olefins Catalyzed by Chiral Ketones

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