Iridium-Catalyzed Enantioselective Fluorination of Racemic, Secondary Allylic Trichloroacetimidates

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• 作者：Qi Zhang ; David P. Stockdale ; Jason C. Mixdorf ; Joseph J. Topczewski ; Hien M. Nguyen
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：September 23, 2015
• 年：2015
• 卷：137
• 期：37
• 页码：11912-11915
• 全文大小：411K
• ISSN：1520-5126

文摘

The Ir-catalyzed enantioselective fluorination of racemic, branched allylic trichloroacetimidates with Et₃N路3HF is a mild and efficient route for selective incorporation of fluoride ion into allylic systems. We herein describe the asymmetric fluorination of racemic, secondary allylic electrophiles with Et₃N路3HF using a chiral-diene-ligated Ir complex. The methodology enables the formation of acyclic fluorine-containing compounds in good yields with excellent levels of asymmetric induction and overcomes the limitations previously associated with the enantioselective construction of secondary allylic fluorides bearing 伪-linear substituents.