Stereoselective synthesis of functionalized gamma-amino esters: azetidinium salts and epoxy esters.
Addition of several lithium ester enolates to chiral 1-aminoalkyl chloromethyl ketones 1 affords enantiomerically pure 3-hydroxyazetidinium salts 3 or 3-(1'-aminoalkyl)-3,4-epoxy esters 4, depending on the reaction conditions. [reaction: see text]
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain. jmcg@sauron.quimica.uniovi.es
Riego
Estela
E
Bernad
Pablo L
PL
D000596:Amino Acids / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D000596:Amino Acids; D001384:Azetidines; D004852:Epoxy Compounds; D007202:Indicators and Reagents