Desymmetrisation of meso-Anhydrides Utilising (S)-Proline Derivatives

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Abstract
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.

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