Synthesis of Polyfluoroalkyl Cyclobutenes from 3-Aza-1,5-enynes via an Aza-Claisen Rearrangement/Cyclization Cascade

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• 作者：Xiaoyi Xin ; Dongping Wang ; Fan Wu ; Chunxiang Wang ; Haolong Wang ; Xincheng Li ; Boshun Wan
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：September 6, 2013
• 年：2013
• 卷：15
• 期：17
• 页码：4512-4515
• 全文大小：257K
• 年卷期：v.15,no.17(September 6, 2013)
• ISSN：1523-7052

文摘

A facile synthetic route to access polyfluoroalkyl functionalized cyclobutenes bearing an exo cyclic double bond from 3-aza-1,5-enynes is reported. The reaction proceeds via a thermal aza-Claisen rearrangement to give an allene-imine intermediate; subsequent cyclization affords the cyclobutene core. The kinetics of the transformation of starting material and the intermediate was studied by ¹H NMR spectroscopy, where a consecutive reaction was revealed.