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Absolute configuration of a diaryldiacyloxy spiroselenurane and resolution of a carbon analog
Author(s) -
Claeson Sofia,
Langer Vratislav,
Allenmark Stig
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:2<71::aid-chir3>3.0.co;2-s
Subject(s) - chemistry , absolute configuration , resolution (logic) , absolute (philosophy) , carbon fibers , stereochemistry , materials science , artificial intelligence , composite number , computer science , composite material , philosophy , epistemology
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 (λ = 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. © 2000 Wiley‐Liss, Inc.