β-Fluoroamphetamines via the Stereoselective Synthesis of Benzylic Fluorides

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• 作者：Alexander J. Cresswell ; Stephen G. Davies ; James A. Lee ; Paul M. Roberts ; Angela J. Russell ; James E. Thomson ; Melloney J. Tyte
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：July 2, 2010
• 年：2010
• 卷：12
• 期：13
• 页码：2936-2939
• 全文大小：223K
• 年卷期：v.12,no.13(July 2, 2010)
• ISSN：1523-7052

文摘

A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF₃·OEt₂ in CH₂Cl₂ at −20 °C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S_N1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.