Synthesis and application of amino alcohol imides as NMR solvating agents for chiral discrimination of carboxylic acids
作者:Mehmet Karakaplan、Basam Jameel
DOI:10.1016/j.tetasy.2016.05.009
日期:2016.8
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.