Organic Chemistry Portal

Abstracts

Search:

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


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.

see article for more examples


see article for more reactions



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