Unique Michael addition-initiated domino reaction for the stereoselective synthesis of functionalized macrolactones from alpha-nitroketones in water.
[reaction: see text]. A unique domino reaction of alpha-nitrocycloalkanones with alpha-alkyl alpha,beta-unsaturated aldehydes in aqueous base was discovered, leading to the one-pot synthesis of hitherto unknown functionalized, bridged, bicyclic lactones containing 10-, 11-, 13-, and 15-membered rings. The structures of these heterocyclic compounds, containing also an unusual 6-hydroxy-1,2-oxazine ring, were determined by spectral and single-crystal X-ray diffraction studies.
Giorgi
Giorgio
G
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
Miranda
Sonia
S
López-Alvarado
Pilar
P
Avendaño
Carmen
C
Rodriguez
Jean
J
Menéndez
J Carlos
JC
D000447:Aldehydes / Q000737:chemistry; D018360:Crystallography, X-Ray; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D008968:Molecular Conformation; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D007659:Ketones; D007783:Lactones; D009574:Nitro Compounds; D014867:Water