4.4 Article

Trapping the elusive aza-oxyallylic cation: new opportunities in heterocycloaddition chemistry

Journal

TETRAHEDRON LETTERS
Volume 55, Issue 34, Pages 4690-4696

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.06.050

Keywords

Cycloaddition; Heterocycles; Nitrogen; Diazo compounds; Bicyclic compounds

Funding

  1. American Chemical Society Petroleum Research Fund Grant [51442-DNI1]
  2. University of Nevada, Reno

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The aza-oxyallylic cation is a reactive intermediate that undergoes a [4+3] cycloaddition with dienes to form seven-membered heterocycles. Although this type of intermediate was proposed over 50 years ago, only recently has experimental evidence been obtained to support its existence. This review highlights the historical studies of aza-oxyallylic cations and their recent development as intermediates for the synthesis of heterocycles and polyheterocyclic scaffolds. (C) 2014 Published by Elsevier Ltd.

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