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Synfacts 2011(11): 1207-1207  
DOI: 10.1055/s-0031-1289219
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Allylic C-H Oxidation

Contributor(s): Mark Lautens, Lei Zhang
P. E. Gormisky, M. C. White*
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

Pd(II)/sulfoxide-catalyzed allylic C-H oxidations offer a unique approach toward functionalizing simple alkenes. As the authors demonstrated previously with allylic C-H aminations (Tetrahedron 2010, 66, 4816; J. Am. Chem. Soc. 2009, 131, 11707), the strategy was applied in the synthesis of anti-1,4-dioxan-2-ones, syn-pyrans, differentiated 1,2-diols, and amino-polyols. These products are highly versatile intermediates in the synthesis of complex polyoxygenated products.