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The Cinchona Primary Amine-Catalyzed Asymmetric Epoxidation and Hydroperoxidation of α,β-Unsaturated Carbonyl Compounds with Hydrogen Peroxide

Olga Lifchits, Manuel Mahlau, Corinna M. Reisinger, Anna Lee, Christophe Farès, Iakov Polyak, Gopinadhanpillai Gopakumar, Walter Thiel and Benjamin List*

*Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1 D-45470, Mülheim an der Ruhr, Germany, Email: listkofo.mpg.de

O. Lifchits, M. Mahlau, C. M. Reisinger, A. Lee, C. Farès, I. Polyak, G. Gopakumar, W. Thiel, B. List, J. Am. Chem. Soc., 2013, 135, 6677-6693.

DOI: 10.1021/ja402058v (free Supporting Information)


Abstract

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds take place. Acyclic enones, cyclic enones, and α-branched enals can be converted. Intermediates have been characterized by MS and NMR. DFT calculations explain the activation of H2O2.

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Catalytic Asymmetric Epoxidation of Cyclic Enones

X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc., 2008, 130, 6070-6071.


Key Words

epoxides, organocatalysis, hydrogen peroxide


ID: J48-Y2013