Highly fluorinated β-amino acids and methods of making and using same

Abstract

Disclosed are compounds having the structure: wherein Rand Rare independently H, alkyl, F, or fluoroalkyl; wherein R, R, R, and Rare independently H, alkyl, F, fluoroalkyl, aryl, or alkenyl; wherein Ris OH, alkoxyl, NH, alkylamino, or dialkylamino; wherein Rand Rare independently H, alkyl, acyl, or alkyloxycarbonyl; wherein R, R, R, R, R, and Rare independently H, alkyl, F, or fluoroalkyl; and wherein C0, C1, C2 and C2' are independently chiral or achiral. Also disclosed are processes for making a fluorinated β-amino acid comprising the steps of: providing a diol; treating the diol with a thionyl halide with oxidative workup; reacting the product with an azide salt to yield an azido group; oxidizing the product to yield a carboxyl group; and reducing the azido group to yield an amino group.