Absolute configuration of a diaryldiacyloxy spiroselenurane and resolution of a carbon analog.
The enantiomers of 3,3'-spirobi(3-selenaphthalide) (2) were obtained via direct separation by liquid chromatography on a chiral stationary phase. Determination of the absolute configuration was made by X-ray crystallography with the use of the anomalous dispersion technique. The first eluted (+)-form (lambda = 302 and 365 nm) of 2 was found to have (S)-configuration. By a comparison of CD-spectra, the same (S)-configuration could be assigned to the (+)-forms of the sulfur (1) and tellurium (7) analogs of 2. An asymmetric dichloro-substituted spirobilactone (4) was also synthesized and separated into its enantiomers. Relative configurations between 4 and its parent compound (3) were established from the corresponding chiroptical data obtained. Chirality 12: 71-75, 2000.
Claeson
S
S
Department of Chemistry, Göteborg University, Göteborg, Sweden.
Langer
V
V
Allenmark
S
S
D002853:Chromatography, Liquid; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D018036:Selenium Compounds / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D018036:Selenium Compounds