Enantioselective synthesis of epoxides having a tetrasubstituted trifluoromethylated carbon center: methylhydrazine-induced aerobic epoxidation of {Beta},{Beta}-disubstituted enones.

Kawai H, Okusu S, Yuan Z, Tokunaga E, Yamano A, Shiro M, Shibata N.

Angew Chem Int Ed Engl. 2013 Feb 18;52(8):2221-5.

Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

 

 

Abstract

 

The unprecedented title reaction is catalyzed by a methylhydrazine/base/organocatalyst (1) system. Biologically attractive epoxides (2) having a tetrasubstituted trifluoromethylated carbon center were obtained with excellent enantioselectivity for the first time. 18O-labeling experiments suggest a mechanism involving the activation of molecular oxygen. MTBE=methyl tert-butyl ether.

 

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