199991-84-9Relevant articles and documents
Preparation and temperature-dependent enantioselectivities of homochiral phenolic crown ethers having aryl chiral barriers: Thermodynamic parameters for enantioselective complexation with chiral amines
Naemura, Koichiro,Nishioka, Kazuyuki,Ogasahara, Kazuko,Nishikawa, Yasushi,Hirose, Keiji,Tobe, Yoshito
, p. 563 - 574 (1998)
Homochiral crown ether (S,S)-1 containing 1-naphthyl groups as chiral barriers together with the phenol moiety was prepared by using (S)-3 as a chiral subunit which was resolved in enantiomerically pure form by lipase- catalyzed enantioselective acylation of (±)-3. Homochiral phenolic crown ether (S,S)-2, containing phenyl groups as chiral barriers, was also prepared from (S)-5 which was derived from (S)-mandelic acid. The association constants for their complexes with chiral amines in CHCl3 were determined at various temperatures by the UV-visible spectroscopic method demonstrating that the crown ethers (S,S)-1 and (S,S)-2 displayed the large Δ(R)-(S)ΔG values of 6.2 and 6.4 kJ mol-1, respectively, towards the amine 21 at 15°C. Thermodynamic parameters for complex formation were also determined and a linear correlation between TΔ(R-S)ΔS and Δ(R-S)ΔH values was observed.
Preparation of homochiral azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: Enantiomer recognition behaviour towards chiral 2-aminoethanol derivatives
Naemura, Koichiro,Ogasahara, Kazuko,Hirose, Keiji,Tobe, Yoshito
, p. 19 - 22 (2007/10/03)
Enantiomerically pure azophenolic crown ethers 1-4 containing (S)- or (R)-1-phenylethane-1,2-diol moieties and (2S,4S)-2,4-dimethyl-3-oxapentane-1,5-diol moiety as a chiral subunit were prepared; crown ethers (S,S,S,S)-1 showed high chiral recognition behaviour in complexation with 2-substituted 2-aminoethanol derivatives.