Solvent-controlled racemic resolution of C3-symmetric trihydroxytribenzotriquinacenes
A racemic C-3-symmetric trihydroxytribenzotriquinacene was resolved on a large scale by fractional crystallization of the corresponding (1S)-camphanic esters, achieving both enantiopure enantiomers (>99% ee) in 35% and 32% yields. The method relies on a distinct solvent-controlled discrimination...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
January 28, 2020
|
| In: |
The journal of organic chemistry
Year: 2020, Volume: 85, Issue: 5, Pages: 3981-3989 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.9b03410 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.9b03410
|
| Author Notes: | Philippe Wagner, Frank Rominger, Thomas Oeser, and Michael Mastalerz |
| Summary: | A racemic C-3-symmetric trihydroxytribenzotriquinacene was resolved on a large scale by fractional crystallization of the corresponding (1S)-camphanic esters, achieving both enantiopure enantiomers (>99% ee) in 35% and 32% yields. The method relies on a distinct solvent-controlled discrimination process between the diastereomers. The enantiopure trihydroxytribenzotriquinacenes were converted into four other enantiopure building blocks, which are valuable precursors for supramolecular and materials chemistry to illustrate the utility of the synthesized compounds. |
|---|---|
| Item Description: | Die Ziffer "3" im Titel ist tiefgestellt Gesehen am 09.04.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.9b03410 |