Enantiomeric recognition of chiral 3,3-bridged-1,1'-binaphthol dimer toward alpha-phenylethylamine and alpha-amino acid ester.
The 1,1'-binaphthol-based dimers with p-phenylenebis(2-ethynyl) spacer, (+)-6 and (+)-2, were synthesized as chiral host compounds. (1)H NMR, UV-vis, and fluorescent titration were used to evaluate the enantiomeric recognition abilities of the chiral host dimers toward the guest amine 7 and alpha-amino acid ester 8. The chiral BINOL-based dimers were found to have good enantiomeric recognition ability. The computer simulation of the host-guest complex molecules was carried out to describe the conformational changes of both naphthyl ring in the molecule of chiral host dimer after complexation with the guest molecule.
Liu
T J
TJ
Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing, P.R. China.
Chen
Y J
YJ
Zhang
K S
KS
Wang
D
D
Guo
D W
DW
Yang
X Z
XZ
D000480:Alkynes / Q000138:chemical synthesis*; D000596:Amino Acids / Q000737:chemistry*; D003198:Computer Simulation; D004952:Esters / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009281:Naphthalenes / Q000138:chemical synthesis*; D009284:Naphthols / Q000138:chemical synthesis*; D010627:Phenethylamines / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
C440213:3,3-(1,4'-diethynylphenyl)bis(1,1'-bi-2-naphthol dimethoxymethyl ether); C440214:3,3-(1,4'-diethynylphenyl)bis(1,1'-bi-2-naphthol); D000480:Alkynes; D000596:Amino Acids; D004952:Esters; D007202:Indicators and Reagents; D009281:Naphthalenes; D009284:Naphthols; D010627:Phenethylamines