Enantiospecific deoxyfluorination of cyclic α-OH-β-ketoesters

We herein report the deoxyfluorination of cyclic alpha-hydroxy-beta-ketoesters using diethylaminosulfur trifluoride (DAST). The reaction proceeds with excellent levels of stereospecificity, giving the configurationally inverted alpha-fluoro-beta-ketoesters in high yields under operationally simple conditions.

Automated summary

The deoxyfluorination of cyclic alpha-hydroxy-beta-ketoesters using DAST reported in this study demonstrates high levels of stereospecificity, resulting in the configurationally inverted alpha-fluoro-beta-ketoesters in high yields under simple operation conditions.