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Synthesis 1995; 1995(9): 1163-1170
DOI: 10.1055/s-1995-4072
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Diastereo- and Regioselective Synthesis of Diquinanes and Related Systems from Tricyclo[3.3.0.02,4]octanes by Chemical Electron Transfer (CET)

Waldemar Adam, Thomas Heidenfelder, Coskun Sahin*
  • *Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany, Fax +49(931)8884756
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Publication Date:
31 December 2000 (online)

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A new synthetic methodology for diquinanes by one-electron oxidation of tricyclo[3.3.0.02,4]octanes and subsequent stereocontrolled rearrangement is provided. The latter compounds are conveniently accessible through acid-catalyzed isopyrazole cycloaddition, followed by hydrogenation and photoextrusion of molecular nitrogen. The oxidative rearrangement of the tricyclooctanes proceeds catalytically and cleanly to afford regio- and diastereoselectively the corresponding diquinanes.

chemical electron transfer - radical cations - catalysis - regio- and diastereoselectivity - oxidative rearrangement