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

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 chi...

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Bibliographic Details
Published inTetrahedron Vol. 70; no. 50; pp. 9545 - 9553
Main Authors Liu, Lu-zhi, He, Chun-huan, Yang, Lin, Huang, Yan, Wu, Qiang, Duan, Wen-gui, Wang, Heng-shan, Pan, Ying-ming
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 16.12.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Enantiomeric recognition
Computational modeling
Levopimaric acid
STATIONARY PHASES
RESOLUTION
Protonated primary amines
METHYL-ESTER
AMINO-ACID
ARJUNOLIC ACID
MOLECULAR RECOGNITION
NMR DISCRIMINATION
(18-CROWN-6)-2,3,11,12-TETRACARBOXYLIC ACID
ENANTIOSELECTIVE RECOGNITION
C-1-Symmetric chiral crown ethers
DERIVATIVES
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Summary: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. (C) 2014 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2014.10.050