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

Sam G. Moss, Ian A. Pocock, Joseph B. Sweeney

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)101-104
Number of pages4
JournalChemistry - A European Journal
Volume23
Issue number1
Early online date22 Nov 2016
DOIs
Publication statusPublished - 1 Jan 2017

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