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The preparation and C-6 epimerisation of benzyl 6α-isocyanopenicillanate is described. By utilising the activating influence of the isocyanide group and a subsequent conversion of this group into an amino-group under mild conditions, 6α-substituted penicillins were thereby prepared. Additionally, several novel rearrangements of these isocyanides are described.
P. H. Bentley, J. P. Clayton, M. O. Boles and R. J. Girven, J. Chem. Soc., Perkin Trans. 1, 1979, 2455 DOI: 10.1039/P19790002455
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