Regioselective and stereospecific synthesis of enantiopure 1,3-oxazolidin-2-ones by intramolecular ring opening of 2-(Boc-aminomethyl)aziridines. Preparation of the antibiotic linezolid.
The amide moiety of several enantiopure unactivated 1-aryl- or 1-alkylaziridine-2-carboxamides were reduced and then N-Boc-protected to afford enantiopure 2-(Boc-aminomethyl)aziridines, which were further converted into enantiopure 5-(aminomethyl)-1,3-oxazolidin-2-ones by means of a stereospecific and fully regioselective BF3.Et2O-promoted intramolecular nucleophilic ring opening. One of these oxazolidinones was transformed into the antibiotic linezolid through a CuI-catalyzed N-arylation reaction at its carbamate moiety.
Morán-Ramallal
Roberto
R
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, E-33071 Oviedo, Spain.
Liz
Ramón
R
Gotor
Vicente
V
D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D000069349:Linezolid; D008968:Molecular Conformation; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000081:Acetamides; D000900:Anti-Bacterial Agents; D001388:Aziridines; D023303:Oxazolidinones; D000069349:Linezolid