Organic Letters 2010-04-02

Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant.

Jayasree Seayad, Abdul Majeed Seayad, Christina L L Chai

Index: Org. Lett. 12(7) , 1412-5, (2010)

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Abstract

Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently in the presence of PhI(OAc)(2) as the oxidant under mild conditions. The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal olefins forming the corresponding vicinal diacetoxy compounds in 70-85% yields and dr (syn/anti) of up to 5.2. Under these conditions, homoallylic alcohols formed the corresponding tetrahydrofuran derivatives in high yields.