Synthesis of Optically Active Organofluorides by Ring Opening of Oxazolidinone-Fused Aziridines

A general method for synthesizing optically active, primary, secondary, and tertiary organofluorides was developed. This chiral pool synthesis utilized the skeleton of arabinose to generate diastereomerically pure 2-oxazolidinone-fused aziridines, which underwent ring opening with a fluoride anion. The adducts, polyoxygenated organofluorides, were useful precursors to various fluorinated compounds, such as fluorinated amino acids.

Automated summary

A general method for synthesizing optically active, primary, secondary, and tertiary organofluorides was developed using the chiral pool synthesis strategy. Diastereomerically pure 2-oxazolidinone-fused aziridines, generated from the skeleton of arabinose, underwent ring opening with a fluoride anion, leading to polyoxygenated organofluorides. These compounds served as useful precursors for various fluorinated compounds, including fluorinated amino acids.