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Can I read Tetra-tert-butyltrioxabicyclo[3.3.1]nonadienedicarboxylic Acid: Optical Resolution, Absolute Configuration and Application in Chiral Discrimination on EtoBox?
Tetra-tert-butyltrioxabicyclo[3.3.1]nonadienedicarboxylic Acid: Optical Resolution, Absolute Configuration and Application in Chiral Discrimination by Jennifer Kremsner; Bianca C. Wallfisch; Ferdinand Belaj; Georg Uray; C. Oliver Kappe; Curt Wentrup; Gert Kollenz is a Chemistry article available to read on EtoBox.
What is Tetra-tert-butyltrioxabicyclo[3.3.1]nonadienedicarboxylic Acid: Optical Resolution, Absolute Configuration and Application in Chiral Discrimination about?
## Abstract The enantiopure bridged bis‐dioxine **4**, a dissymmetric dicarboxylic acid exhibiting axial chirality, can easily be synthesized and serve as host for separating and/or transporting chiral guest molecules. Racemic **4** gives with (__R__)‐ and (__S__)‐1‐phenylethylamine the corresponding pure diastereomeric salts **7** and **8**. The absolut configuration of the diacid **4** in the diastereomeric salt **7** containing (__R__)‐1‐phenylethylamine was confirmed to be __R__ by X‐ray crystal structure analysis, which also confirmed its concave nature. Release of the acid‐sensitive pure enantiomers (__R__)‐**4** as well as (__S__)‐**4** was achieved conveniently by use of dry flash‐chromatography on silica. The CD spectrum shows a positive Cotton effect of the (__S__)‐enantiomer at 206 nm. The enantiomeric purity was proved by ^1^H NMR discrimination of the diastereomeric salts with (__R__,__R__)‐1,2‐bis(4‐methoxyphenyl)ethane‐1,2‐diamine as the base. The dicarboxylic acid (__R__)‐**4** can be used as chiral auxiliary as demonstrated by the difficult resolution of racemic__N__,__N__′‐di‐__tert__‐butyl‐1,2‐bis(4‐methoxyphenyl)ethane‐1,2‐diamine **9**.(© Wiley‐VCH Verlag GmbH
Who reads Tetra-tert-butyltrioxabicyclo[3.3.1]nonadienedicarboxylic Acid: Optical Resolution, Absolute Configuration and Application in Chiral Discrimination?
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- Author
- Jennifer Kremsner; Bianca C. Wallfisch; Ferdinand Belaj; Georg Uray; C. Oliver Kappe; Curt Wentrup; Gert Kollenz
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 1434-193X)
- Published
- 2008
- Language
- EN
- Field
- Chemistry (Physical Sciences)