Stereoselective synthesis of trifluoromethyl analogues of polyhydroxypyrrolidines

Abstract

Incorporation of fluorine atoms into organic molecules significantly enhances many of their properties, such as solubility, metabolic stability, and bioavailability. Among organofluorine molecules, trifluoromethylated compounds play a unique and important role in agricultural and medicinal chemistry. An efficient strategy for the synthesis of a variety of trifluoromethylated polyhydroxypyrrolidines is described. This strategy involves a diastereoselective nucleophilic addition reaciton of trimethyl(trifluoromethyl)silane to sugar-derived cyclic nitrones followed by reductive N–O bond cleavage and removal of benzyl groups.