An in situ formed porphyrin-inspired iron complex that catalyzes asymmetric epoxidation of di- and trisubstituted enones is described. The reaction provides highly enantioenriched alpha,beta-epoxyketones (up to 99% ee). The practical utility of the new catalyst system is demonstrated by the gram-scale synthesis of optically pure epoxide. Hammett analysis suggests that the transition state of the reaction is electron-demanding and the active oxidant is electrophilic.
1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China 2.Chinese Acad Sci, Dalian Natl Lab Clean Energy, Dalian 116023, Peoples R China
Recommended Citation:
Dai, Wen,Li, Guosong,Chen, Bo,et al. A Porphyrin-Inspired Iron Catalyst for Asymmetric Epoxidation of Electron-Deficient Olefins[J]. ORGANIC LETTERS,2015,17(4):904-907.
