Science of Synthesis

Gouverneur, V.; Lozano, O., Science of Synthesis: Stereoselective Synthesis, (2011) 3, 853.

For the preparation of complex fluorinated molecules featuring multiple stereocenters, the fluorination typically relies on the presence of existing stereocenters to induce stereocontrol. This strategy is most often used for installing the fluorine substituent α to a carbonyl group that is preactivated as a silyl enol ether or metal enolate. Various biologically important fluorinated compounds, e.g. steroids, β-lactams, ketone peptide isosteres, and nucleosides have been prepared using this approach. The diastereoselective fluorination of ketones and carboxylic acids bearing either a chiral auxiliary or a removable stereodirecting group is also a reliable route to access enantioenriched α-fluoro carbonyl derivatives. This method provides fluorinated building blocks amenable to further functional manipulation. Functionalized organosilanes also provide suitable templates for diastereoselective fluorination reactions.[‌11‌]

References

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• 8.Meeeee-Meee, (8888) 8/8, 888.