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Synlett 1997; 1997(12): 1478-1480
DOI: 10.1055/s-1997-1060
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Synthesis of Enantiomerically Pure, All Syn, Tetra and Pentasubstituted Cyclopentanes by the Desymmetrisation of Endo-Norborn-5-ene-2,3-Dicarboxylic Anhydrides

Iwan G. Jones1 , Wyn Jones2 , Michael North3
  • 1Department of Chemistry, University of Wales, Bangor, Gwynedd, LL57 2UW
  • 2Peboc Division of Eastman Chemical (UK) Ltd., Industrial Estate, Llangefni, Anglesey, Gwynedd, LL77 7YQ
  • 3Department of Chemistry, University of Wales, Bangor, Gwynedd, LL57 2UW, Email m.north@bangor.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Ozonolysis of diastereomerically pure norbornene derivatives incorporating methyl (S)-prolinate provides a route for the synthesis of enantiomerically pure cyclopentanes bearing four or five substituents all oriented syn to one another.

cyclopentane - anhydride - desymmetrisation - proline - ozonolysis