Synthesis of chiral crownophanes having two phenolic groups via tandem claisen rearrangement and their chiral recognition

Citation
H. Tokuhisa et al., Synthesis of chiral crownophanes having two phenolic groups via tandem claisen rearrangement and their chiral recognition, J INCL P MA, 39(3-4), 2001, pp. 347-352
Citations number
15
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
ISSN journal
1388-3127 → ACNP
Volume
39
Issue
3-4
Year of publication
2001
Pages
347 - 352
Database
ISI
SICI code
1388-3127(200104)39:3-4<347:SOCCHT>2.0.ZU;2-P
Abstract
Asymmetric crownophanes having a chiral binaphthyl unit and two phenolic hy droxyl groups were thermally synthesized from the corresponding macrocyclic ethers via tandem Claisen rearrangement. Circular dichroism (CD) spectrosc opic studies and HPLC experiments confirmed that little racemization of the se crownophanes occurred during the thermal rearrangement. The association constants for the interaction of the chiral crownophanes with the enantiome rs of phenylethylamine, phenylglycinol, and phenylalaninol were determined by a H-1 NMR titration method in CD2Cl2. As a result, the 27 membered crown ophane has some chiral recognition for phenylglycinol.