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  • Title: Synthesis of Small 3-Fluoro- and 3,3-Difluoropyrrolidines Using Azomethine Ylide Chemistry.
    Author: McAlpine I, Tran-Dubé M, Wang F, Scales S, Matthews J, Collins MR, Nair SK, Nguyen M, Bian J, Alsina LM, Sun J, Zhong J, Warmus JS, O'Neill BT.
    Journal: J Org Chem; 2015 Jul 17; 80(14):7266-74. PubMed ID: 26057617.
    Abstract:
    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 α,β-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.
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