ChemInform Abstract: From Amino Acids to Fluorine‐Containing Carbohydrates: De novo Synthesis of 2‐Amino‐4‐fluoroxylose and ‐lyxose.

Synthesis of (2S)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination

“…21 Therefore, the oxazolidinone was first cleaved by careful treatment with 0.5 equiv of sodium ethoxide at −78 °C to afford ester 14 in 91% yield as a single diastereomer. 22 Compound 14 was finally cyclized in acidic conditions followed by 5-TBSprotection to give the 2-chlorolactone 15 which was identified as the (2R,3R) isomer by Xray crystallography (Figure 2). Fluorination of oxazolidinone derivative 13 was attempted using 1.3 equiv of LiHMDS and 1.5 equiv of NFSI (Scheme 3), but unfortunately no fluorinated product was observed under these standard conditions.…”