Final published version
Research output: Contribution to Journal/Magazine › Journal article
<mark>Journal publication date</mark> | 1/01/2017 |
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<mark>Journal</mark> | Chemistry - A European Journal |
Issue number | 1 |
Volume | 23 |
Number of pages | 4 |
Pages (from-to) | 101-104 |
Publication Status | Published |
Early online date | 29/11/16 |
<mark>Original language</mark> | English |
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.