Synthesis of Small 3-Fluoro- and 3,3-Difluoropyrrolidines Using Azomethine Ylide Chemistry

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• 作者：Indrawan McAlpine ; Michelle Tran-Dub茅 ; Fen Wang ; Stephanie Scales ; Jean Matthews ; Michael R. Collins ; Sajiv K. Nair ; Mary Nguyen ; Jianwei Bian ; Luis Martinez Alsina ; Jianmin Sun ; Jiaying Zhong ; Joseph S. Warmus ; Brian T. O鈥橬eill
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：July 17, 2015
• 年：2015
• 卷：80
• 期：14
• 页码：7266-7274
• 全文大小：433K
• ISSN：1520-6904

文摘

Here, we report accessing small 3-fluoropyrrolidines and 3,3-difluoropyrrolidines through a 1,3-dipolar cycloaddition with a simple azomethine ylide and a variety of vinyl fluorides and vinyl difluorides. We demonstrate that vinyl fluorides within 伪,尾-unsaturated, styrenyl and even enol ether systems can participate in the cycloaddition reaction. The vinyl fluorides are relatively easy to synthesize through a variety of methods, making the 3-fluoropyrrolidines very accessible.