Preparation and temperature-dependent enantioselectivities of homochiral phenolic crown ethers having aryl chiral barriers: Thermodynamic parameters for enantioselective complexation with chiral amines

Koichiro Naemura*, Kazuyuki Nishioka, Kazuko Ogasahara, Yasushi Nishikawa, Keiji Hirose, Tobe Yoshito

*此作品的通信作者

研究成果: Article同行評審

42 引文 斯高帕斯(Scopus)

摘要

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.

原文English
頁(從 - 到)563-574
頁數12
期刊Tetrahedron Asymmetry
9
發行號4
DOIs
出版狀態Published - 27 二月 1998

指紋

深入研究「Preparation and temperature-dependent enantioselectivities of homochiral phenolic crown ethers having aryl chiral barriers: Thermodynamic parameters for enantioselective complexation with chiral amines」主題。共同形成了獨特的指紋。

引用此