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Tandem Aryne-Capture/Sigmatropic Rearrangement as a Metal-Free Entry to Functionalized N-Aryl Pyrrolidines

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<mark>Journal publication date</mark>1/01/2017
<mark>Journal</mark>Chemistry - A European Journal
Issue number1
Volume23
Number of pages4
Pages (from-to)101-104
Publication statusPublished
Early online date29/11/16
Original languageEnglish

Abstract

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.

Bibliographic note

Author was employed at another UK HEI at the time of submission and was deposited at Huddersfield University Repository, see link http://eprints.hud.ac.uk/id/eprint/31857/