Novel C-1-symmetric chiral crown ethers bearing rosin acids groups: synthesis and enantiomeric recognition for ammonium salts

作者：Liu, Lu-zhi; He, Chun-huan; Yang, Lin; Huang, Yan; Wu, Qiang; Duan, Wen-gui; Wang, Heng-shan^*; Pan, Ying-ming

来源：Tetrahedron, 2014, 70(50): 9545-9553.

DOI：10.1016/j.tet.2014.10.050

• C-1-Symmetric chiral crown ethers
• Levopimaric acid
• Protonated primary amines
• Enantiomeric recognition
• Computational modeling

Four types of novel C-1-symmetric chiral crown ethers including 28-crown-8, 20-crown-6, 17-crown-5 and 14-crown-3 (9a-m) were synthesized and their enantiodiscriminating abilities with protonated primary amines (10-14) were examined by H-1 NMR spectroscopy. 20-crown-6 crown ethers exhibited good chiral recognition properties toward these guests and showed different complementarity to some chiral guests, indicating that 20-crown-6 crown ethers could be used as a chiral NMR solvating agent to determine the enantiopurity of these guests. In addition, the binding model and binding site between the hosts and guests were also studied by the computational modeling and experimental calculation.

• 出版日期2014-12-16
• 单位广西师范大学; 广西壮族自治区中医药研究院; 广西大学