Highly selective acylations using a biomimetic strategy

Article abstract of DOI:10.1016/S0040-4039(00)77663-5

Rapid, high yield acylation of thiol-bearing amines by one equivalent of thioacid may be carried out at 1 mM in the presence of large excesses of other primary amines. Silver ion, known to activate thioacids toward nucleophilic attack, simultaneously also serves as a binding site to deliver a thiol-tethered amine. An interesting dependence of yields and selectivity on [Ag+] was found, as well as a significant effect of chloride.