Stereoselective synthesis of alpha-monofluorinated phosphonate mimetics of naturally occurring phosphoserine and phosphothreonine, via electrophilic fluorination of lithiated bis-lactim ethers.
Electrophilic fluorinations of lithiated bis-lactim ethers derived from cyclo-[L-AP4-D-Val] allow a direct access to alpha-monofluorinated phosphonate mimetics of naturally occurring phosphoserine and phosphothreonine, in enantiomerically pure form and suitably protected for solid-phase peptide synthesis.
Ruiz
María
M
Departamento de Química Fundamental, Universidade da Coruña, Campus da Zapateira, s/n, 15071 A Coruña, Spain. ruizpr@udc.es
Ojea
Vicente
V
Quintela
José M
JM
Guillín
Juan J
JJ
D018360:Crystallography, X-Ray; D004987:Ethers / Q000737:chemistry; D005461:Fluorine; D007202:Indicators and Reagents; D007769:Lactams / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D010768:Phosphoserine / Q000737:chemistry*; D010769:Phosphothreonine / Q000737:chemistry*; D013237:Stereoisomerism
D004987:Ethers; D007202:Indicators and Reagents; D007769:Lactams; D063065:Organophosphonates; D010769:Phosphothreonine; D010768:Phosphoserine; D005461:Fluorine