Shi epoxidation

Shi epoxidation

The Shi epoxidation is a chemical reaction described as an asymmetric epoxidation of olefins with oxone (potassium peroxymonosulfate) and a fructose-derived catalyst (1).Ref|Wang1997Ref|Frohn2000

This procedure generates epoxides with high enantiomeric excesses from trans-disubstituted alkenes and trisubstituted alkenes. Cis-disubstituted alkenesRef|Tian2000 and styrenesRef|Tian2001 are asymmetrically epoxidized using a similar catalyst.

References

# "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)
# Frohn, M.; Shi, Y. "Synthesis" 2000, "14", 1979-2000. (Review)
# Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. "J. Am. Chem. Soc." 2000, "122", 11551-11552. (DOI|10.1021/ja003049d)
# Tian, H.; She, X.; Xu, J.; Shi, Y. "Org. Lett." 2001, "3", 1929-1931. (DOI|10.1021/ol010066e)

ee also

*Sharpless epoxidation


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