Shi epoxidation

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The Shi epoxidation is a chemical reaction described as an asymmetric epoxidation of olefins with oxone and a fructose-derived catalyst (1).^[1][2]

This procedure generates epoxides with high enantiomeric excesses from trans-disubstituted alkenes and trisubstituted alkenes. Cis-disubstituted alkenes^[3] and styrenes^[4] are asymmetrically epoxidized using a similar catalyst.

[edit] References

1. ↑  An Efficient Catalytic Asymmetric Epoxidation Method Zhi-Xian Wang, Yong Tu, Michael Frohn, Jian-Rong Zhang, and Yian Shi J. Am. Chem. Soc. 1997, 119(46), 11224-11235. (DOI:10.1021/ja972272g)
2. ↑  Frohn, M.; Shi, Y. Synthesis 2000, 14, 1979-2000. (Review)
3. ↑  Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551-11552. (DOI:10.1021/ja003049d)
4. ↑  Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929-1931. (DOI:10.1021/ol010066e)

[edit] See also

• Sharpless epoxidation