Abstract
AbstractAn unexpected lability of the benzyloxycarbonyl (Z) protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilises the tetrahedral intermediate formed after nucleophilic addition of hydroxide to the carbonyl of the Z group. This effect operates in N‐protected tripeptides and tetrapeptides but Z‐protected dipeptides are stable under the same conditions due to blockage of the vicinal amide NH by intramolecular H‐bonding with the terminal carboxylate moiety.
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