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syn-Diacetoxylation of Alkenes with Palladium and Molecular Oxygen
A. Wang, H. Jiang*, H. Chen
South China University of Technology, Guangzhou, P. R. of China
25 May 2009 (online)
While various palladium-catalyzed methods for alkene difunctionalization have appeared recently in the literature, most of these protocols require the use of PhI(OAc)2 as oxidant to oxidize Pd(II) to Pd(IV). In the present study the authors report the first example of a palladium-catalyzed diacetoxylation of alkenes using direct oxygen-mediated Pd(II)/Pd(IV) oxidation. An array of cis- and trans-disubstituted alkenes is efficiently diacetylated to provide syn products in high yields and diastereoselectivities.