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One-Pot Oxidation/Isomerization of Z-Allylic Alcohols with Oxygen as Stoichiometric Oxidant

Daniel Könning, Wolf Hiller and Mathias Christmann*

*Institute of Chemistry and Biochemistry, FU Berlin, Takustr. 3, 12195 Berlin, Email: mathias.christmannfu-berlin.de

D. Könning, W. Hiller, M. Christmann, Org. Lett., 2012, 14, 5258-5261.

DOI: 10.1021/ol302420k (free Supporting Information)


Abstract

A method for generating (E)-α,β-unsaturated aldehydes from Z- or E-allylic alcohols involves a Cu-catalyzed oxidation followed by an organocatalytic Z/E-isomerization with N,N-dimethylaminopyridine (DMAP).

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Key Words

enals, oxygen, TEMPO, oxidation, isomerization


ID: J54-Y2012-3350