Stereoselective synthesis of α-monofluorinated phosphonate mimetics of naturally occurring phosphoserine and phosphothreonine, via electrophilic fluorination of lithiated bis-lactim ethers

Abstract

Electrophilic fluorinations of lithiated bis-lactim ethers derived from cyclo-[L-AP4-D-Val] allow a direct access to α-monofluorinated phosphonate mimetics of naturally occurring phosphoserine and phosphothreonine, in enantiomerically pure form and suitably protected for solid-phase peptide synthesis.