Solvent-controlled racemic resolution of C3-symmetric trihydroxytribenzotriquinacenes

• Verfasst von: Wagner, Philippe [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Oeser, Thomas [VerfasserIn]
• Verfasst von: Mastalerz, Michael [VerfasserIn]
• Titel: Solvent-controlled racemic resolution of C3-symmetric trihydroxytribenzotriquinacenes
• Verf.angabe: Philippe Wagner, Frank Rominger, Thomas Oeser, and Michael Mastalerz
• E-Jahr: 2020
• Jahr: January 28, 2020
• Umfang: 9 S.
• Fussnoten: Die Ziffer "3" im Titel ist tiefgestellt ; Gesehen am 09.04.2020
• Titel Quelle: Enthalten in: The journal of organic chemistry
• Ort Quelle: [S.l.] : American Chemical Society, 1936
• Jahr Quelle: 2020
• Band/Heft Quelle: 85(2020), 5, Seite 3981-3989
• ISSN Quelle: 1520-6904
• DOI: doi:10.1021/acs.joc.9b03410
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1694334759

Abstract

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.