A Porphyrin-Inspired Iron Catalyst for Asymmetric Epoxidation of Electron-Deficient Olefins

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• 作者：Wen Dai ; Guosong Li ; Bo Chen ; Lianyue Wang ; Shuang Gao
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 20, 2015
• 年：2015
• 卷：17
• 期：4
• 页码：904-907
• 全文大小：343K
• ISSN：1523-7052

文摘

An in situ formed porphyrin-inspired iron complex that catalyzes asymmetric epoxidation of di- and trisubstituted enones is described. The reaction provides highly enantioenriched 伪,尾-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.