Novel synthesis of pseudopeptides bearing a difluoromethyl group by Ugi reaction and desulfanylation

Beilstein J Org Chem. 2011:7:1070-4. doi: 10.3762/bjoc.7.123. Epub 2011 Aug 8.

Abstract

Thirteen difluoromethyl-containing pseudopeptides were synthesized by Ugi reaction using the novel building block 2,2-difluoro-2-(phenylthio)acetic acid (2) as one component, followed by removal of the phenylsulfanyl protecting group in the presence of tributyltin hydride and azobisisobutyronitrile.

Keywords: Ugi reaction; difluoromethyl functionality; gem-difluoromethylene-containing acid; pseudopeptides; reductive cleavage.