Synthesis and application of amino alcohol imides as NMR solvating agents for chiral discrimination of carboxylic acids
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Tarih
2016
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Pergamon-Elsevier Science Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
A series of amino alcohol imides 2-8 have been synthesized from commercially available starting materials by regioselective ring opening reaction of epoxides with chiral amines. Compounds 2-8 were tested as chiral solvating agents (CSAs) for enantiomeric discrimination of biological important carboxylic acids. C-2-Symmetric (S,R,R,S)-3 was found to be a satisfactory CSA for mandelic acid with Delta Delta delta of 24.8 Hz. CSA (S, S)-5 exhibited the best enantiomeric discrimination for alpha-phenyl-alpha-methoxyacetic acid with Delta Delta delta of 32 Hz. Enantiomeric differentiated values found for mandelic acid, o-chloro mandelic acid, ibuprofen and naproxen are 7.2, 4.4, 2 and 3 Hz respectively. (C) 2016 Elsevier Ltd. All rights reserved.
Açıklama
Anahtar Kelimeler
[No Keyword]
Kaynak
Tetrahedron-Asymmetry
WoS Q Değeri
Q2
Scopus Q Değeri
N/A
Cilt
27
Sayı
14-15
