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Synthesis 1996; 1996(3): 393-398
DOI: 10.1055/s-1996-4223
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Desymmetrisation of meso-Anhydrides Utilising (S)-Proline Derivatives

Thomas Albers, Stefano C.G. Biagini, David E. Hibbs, Michael B. Hursthouse, K. M. Abdul Malik, Michael North* , Eugenio Uriarte, Guiseppe Zagotto
  • *Department of Chemistry, University of Wales, Bangor, Gwynedd, LL57 2UW, UK, E-mail CHS029@bangor.ac.uk
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Publication Date:
31 December 2000 (online)

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meso-Anhydrides derived from norbornanes and norbornenes, undergo an asymmetric ring opening upon treatment with (S)-proline derivatives, to give amido acids with moderate to excellent enantiomeric excesses. A cyclopropane derived anhydride was also desymmetrised in this way, whilst cyclohexyl derived anhydrides gave a 1:1 mixture of diastereomers. The origin of the desymmetrisation is explained by a model based on steric interactions in the transition state.

proline methyl ester - meso-anhydride - desymmetrise - norbornene - amido acid

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