Optical resolution of phosphorus containing calix[4]arenes by additive RP HPLC method

Authors
Kalchenko, OI Tairov, MO Vysotsky, MO Lipkowski, J Kalchenko, VI
Citation
Oi. Kalchenko et al., Optical resolution of phosphorus containing calix[4]arenes by additive RP HPLC method, ENANTIOMER, 5(3-4), 2000, pp. 385-390
Citations number
23
Categorie Soggetti
Chemistry
Journal title
ENANTIOMER
ISSN journal
10242430 → ACNP
Volume
5
Issue
3-4
Year of publication
2000
Pages
385 - 390
Database
ISI
SICI code
1024-2430(2000)5:3-4<385:OROPCC>2.0.ZU;2-Y
Abstract
The RP HPLC method (LiChrosorb RP18 or Separon SGX C-18 column, acetonitril e-water 86:14 v/v mobile phase) was applied for enantiomeric separation of topologically chiral 5-bromo-25,26-bis(diethoxyphosphoryl)calix[4]arene 9 o r 25-ethyl-26-dihydroxyphosphoryl-calix[4]arene 5. Separation of calixarene 9 was achieved by the addition of D-(-)-tartaric acid which formed hydroge n bonded diastereomeric associates with 9 to the mobile phase. Calixareneph osphoric acid 5 was transformed into diastereomeric salt 6 by addition of L -(-)-alpha -phenylethylamine before RP HPLC separation.