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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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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Abstract 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.
AbstractList 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.
Author He, Chun-huan
Pan, Ying-ming
Yang, Lin
Duan, Wen-gui
Wang, Heng-shan
Huang, Yan
Liu, Lu-zhi
Wu, Qiang
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Issue 50
Keywords 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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Snippet 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...
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StartPage 9545
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Novel C-1-symmetric chiral crown ethers bearing rosin acids groups: synthesis and enantiomeric recognition for ammonium salts
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