A- and B-fluorinated aminophosphonates–Synthesis and properties

GRAPHICAL ABSTRACT

ABSTRACT

Interest in synthesis of fluorinated aminophosphonates has grown significantly in recent years due to their promising applications in medicinal and bioorganic chemistry. We report herein efficient and general methods for the synthesis of α- and β-monofluorinated aminophosphonates. Series of β-fluoro aminophosphonates were prepared in nucleophilic DAST-mediated fluorination of α-hydroxyphosphonates. The Horner–Wadsworth–Emmons reaction between carbonyl compounds containing an amino group and lithiated tetraethyl fluoromethylenediphosphonate was used in the synthesis of α-fluorinated-γ-aminophosphonates. Futhermore, this protocol was efficiently applied in the synthesis of dipeptide analogues α-fluorinated-γ-aminophosphonates.

Keywords:

• Fluorinated aminophosphonates
• nucleophilic fluorination
• Horner–Wadsworth–Emmons reaction