Diastereoselective Mannich Reactions Using Fluorinated Ketones: Synthesis of Stereogenic Carbon–Fluorine Units

A diastereoselective
Mannich reaction of simple α-fluoro
ketones with N-tert-butyl­sulfinyl­imines
was developed. This method provides a concise route to a variety of
structurally diverse α-fluoro-β-amino ketones containing
fluorinated stereogenic carbon centers; good yields and high diastereoselectivities
were achieved. This method uses readily accessible starting materials
and has a broad substrate scope: cyclic and linear α-fluoro
ketones and fluoromethyl ketones are all suitable substrates.