HIGHLY FLUORINATED ß-AMINO ACIDS AND METHODS OF MAKING AND USING SAME

摘要

Disclosed are compounds having the structure: wherein R^la and R^lb are independently H, alkyl, F, or fluoroalkyl; wherein R^2a, R^2b, R^2a', and R^2b are independently H, alkyl, F, fluoroalkyl, aryl, or alkenyl; wherein R³ is OH, alkoxyl, NH₂, alkylamino, or dialkylamino; wherein R^4a and R^4b are independently H, alkyl, acyl, or alkyloxycarbonyl; wherein R₁₁, R₁₂, R₁₃, R₂₁, R₂₂, and R₂₃ are independently H, alkyl, F, or fluoroalkyl; and wherein CO, Cl, C2, and C2' are independently chiral or achiral. Also disclosed are processes for making a fluorinated ß-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. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.