4.8 Article

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

Journal

ORGANIC LETTERS
Volume 25, Issue 1, Pages 190-194

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c04042

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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.
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.

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