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Synfacts 2009(6): 0651-0651  
DOI: 10.1055/s-0029-1217201
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

syn-Diacetoxylation of Alkenes with Palladium and Molecular Oxygen

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
A. Wang, H. Jiang*, H. Chen
South China University of Technology, Guangzhou, P. R. of China
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

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.