Moss, Sam G., Pocock, Ian A. and Sweeney, Joseph B. (2017) Tandem Aryne-Capture/Sigmatropic Rearrangement as a Metal-Free Entry to Functionalized N -Aryl Pyrrolidines. Chemistry - A European Journal, 23 (1). pp. 101-104. ISSN 0947-6539

We report a new method for the synthesis of novel N-aryl proline analogues. By reacting an aryne precursor with N-(2-malonyl) tetrahydropyridines in the presence of tetrabutylammonium fluoride (TBAF), a tandem aryne-capture/anion isomerisation/[2,3]-sigmatropic rearrangement is induced, leading to good yields of 3-substituted N-aryl-2-acylpyrrolidines. These products are known subunits of biological probes, sensors and drug-like fragments, and are not easily accessed directly by other methods. The reaction is also notable as the first [2,3]-rearrangement of cyclic ammonium ylides at room temperature.

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