Elsevier

Tetrahedron

Volume 54, Issue 17, 23 April 1998, Pages 4319-4326
Tetrahedron

Convenient asymmetric (salen)Mn(III)-catalyzed epoxidation of unfunctionalized alkenes with hydrogen peroxide using carboxylate salt cocatalysts

https://doi.org/10.1016/S0040-4020(98)00145-8Get rights and content

Abstract

Asymmetric epoxidation of unfunctionalized alkenes is reported using chiral (salen)Mn(III) complexes 1–5 together with a carboxylate salt cocatalyst in the presence of either aqueous H2O2 or anhydrous urea-H2O2 adduct as oxidant. Several simple soluble salts (acetates, formates, benzoates) were studied all giving good yields of epoxides with moderate to excellent enantioselectivity. For example, 1,1-diphenyl-1-propene was converted into the corresponding epoxide of 96 % ee in 84 % yield. Generally, this epoxidation method gave better results than a previously described system using nitrogen heterocycles as cocatalysts.

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