Synthesis of fluoroalkylated beta-aminophosphonates and pyridines from primary beta-enaminophosphonates.
A simple and efficient stereoselective synthesis of fluorine containing beta-aminophosphonates by reduction of beta-enaminophosphonates is described. Reduction with sodium cyanborohydride in the presence of zinc chloride and the catalytic hydrogenation of beta-enaminophosphonates gives beta-aminophosphonates. beta-Enaminophosphonates are also used as intermediates for the regioselective synthesis of fluoroalkyl-substituted pyridines.
Palacios
Francisco
F
Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Vitoria, Spain. francisco.palacios@ehu.es
Ochoa de Retana
Ana M
AM
Oyarzabal
Julen
J
Pascual
Sergio
S
Fernández de Trocóniz
Guillermo
G
D000478:Alkylation; D005461:Fluorine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization
D063065:Organophosphonates; D011725:Pyridines; D005461:Fluorine