Facile synthesis of a C4-symmetrical inherently chiral calix[4]arene†
Date
2021-09
Journal Title
Journal ISSN
Volume Title
Publisher
Royal Society of Chemistry
Abstract
Inherently chiral calix[4]arenes with C4-symmetry are extremely rare and difficult to synthesise, severely hampering any effort to expand on their potential as chiral supramolecular catalysts and building blocks. Herein we report a reaction of a tetracarbamate calix[4]arene with NBS which results in a high yield of an inherently chiral calix[4]arenes with C4-symmetry. Furthermore, employing a chiral N-Boc proline moiety allows for separation of the diastereomers formed, thus obtaining the pure enantiomers after hydrolysis. The enantiomers could be assigned based on the CD spectra and DFT calculated values.
Description
CITATION: Hodson, L. et al. 2021. Facile synthesis of a C4-symmetrical inherently chiral calix[4]arene†. Chemical Communications 57(84):4 pages. doi.10.1039/D1CC04607A
The original publication is available at: rsc.org
The original publication is available at: rsc.org
Keywords
Enantioselective catalysis, Facile synthesis, Calixarenes, Chirality
Citation
Hodson, L. et al. 2021. Facile synthesis of a C4-symmetrical inherently chiral calix[4]arene†. Chemical Communications 57(84):4 pages. doi.10.1039/D1CC04607A