Alkoxyacetyl (AAc) group as a useful linker for organic synthesis on poly(ethylene glycol) support

An alkoxyacetyl group (AAc) group was found to be an efficient linker for high-throughput synthesis of small molecules on a soluble polymer support. The linker allows high-yield loading of alcohols and phenols either by conventional carbodiimide-mediated esterification or transesterification using Yb(OTf)3. Chemoselective cleavage to release small molecules is attained also by Yb(OTf)3 or TMSCHN2. The preparation, protocols for loading and releasing of small molecules, and an application to the Ugi four-component coupling reaction are reported.