Transformations using benzyl 6-isocyanopenicillanate

Abstract

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.