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

✍ Scribed by Pekka Pietikäinen


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
511 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis


Asymmetric epoxidation of unfunctionalized alkenes is reported using chiral (salen)Mn(III) complexes 1-$ together with a carboxylate salt cocatalyst in the presence of either aqueous H202 or anhydrous urea-H202 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,l-diphenyl-l-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 heteroeycles as cocatalysts.


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