Stereoselective NaN3-catalyzed halonitroaldol-type reaction of azetidine-2,3-diones in aqueous media.
Azetidine-2,3-diones (alpha-oxo-beta-lactams) and bromonitromethane undergo coupling in aqueous media in the presence of catalytic amounts of sodium azide. The stereoselectivity of the process was generally good, proceeding with reasonable anti : syn ratios under substrate control. On this basis, a simple and fast protocol for the synthesis of the potentially bioactive 3-substituted 3-hydroxy-beta-lactam moiety has been developed. Besides, 2-azetidinone-tethered 1-halo-1-nitroalkan-2-ols are quite useful building blocks; for example, reactions of the above nitrobromohydrins provided spiranic and fused bicyclic-beta-lactams.
Alcaide
Benito
B
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Luna
Amparo
A
Torres
M Rosario
MR
D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D019810:Sodium Azide / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry; D047090:beta-Lactams / Q000138:chemical synthesis / Q000737:chemistry*
D012996:Solutions; D047090:beta-Lactams; D014867:Water; D019810:Sodium Azide