Organic Chemistry Portal



Guanidine-Urea Bifunctional Organocatalyst for Asymmetric Epoxidation of 1,3-Diarylenones with Hydrogen Peroxide

Shinji Tanaka, Kazuo Nagasawa*

*Department of Biotechnology and Life Science, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Email:

S. Tanaka, K. Nagasawa, Synlett, 2009, 667-670.

DOI: 10.1055/s-0028-1087811

see article for more reactions


A highly enantioselective catalytic epoxidation of α,β-unsaturated diaryl enones was achieved with high chemical yield by using aqueous hydrogen peroxide in the presence of a guanidine-urea bifunctional organocatalyst. The catalyst performs cooperatively by interaction of the guanidine group with hydrogen peroxide and the urea group with the enone or vice versa.

see article for more examples

Key Words

guanidine, urea, organocatalysis, hydrogen peroxide, epoxidation, electron-deficient olefin

ID: J60-Y2009-0800