Optical resolution of phosphorus containing calix[4]arenes by additive RP HPLC method.
The RP HPLC method (LiChrosorb RP18 or Separon SGX C18 column, acetonitrile-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 or 25-ethyl-26-dihydroxyphosphoryl-calix[4]arene 5. Separation of calixarene 9 was achieved by the addition of D-(-)-tartaric acid which formed hydrogen bonded diastereomeric associates with 9 to the mobile phase. Calixarenephosphoric acid 5 was transformed into diastereomeric salt 6 by addition of L-(-)-alpha-phenylethylamine before RP HPLC separation.
Kalchenko
O I
OI
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya, 5 553660, Kiev-94, Ukraine.
Tairov
M O
MO
Vysotsky
M O
MO
Lipkowski
J
J
Kalchenko
V I
VI
D047250:Calixarenes; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D006860:Hydrogen Bonding; D046911:Macromolecular Substances; D009682:Magnetic Resonance Spectroscopy; D010758:Phosphorus / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D046911:Macromolecular Substances; D047250:Calixarenes; D010758:Phosphorus