Polymer-supported silyl enol ethers. Synthesis and reactions with imines for the preparation of an amino alcohol library

Article abstract of DOI:10.1016/0040-4039(96)00435-2

Polymer-supported silyl enol ethers (thioketene silyl acetals) were prepared from chloromethyl copoly-(styrene-1%-divinylbenzene) resin. The silyl enol ethers reacted with imines in the presence of a catalytic amount of scandium triflate (Sc(OTf)₃) to afford β-amino thioesters, which were reduced to amino alcohols in good yields. These reactions provide a convenient method for the preparation of an amino alcohol library.