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Synthesis and application of amino alcohol imides as NMR solvating agents for chiral discrimination of carboxylic acids

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. C2-Symmetric (S,R,R,S)-3 was found to be a satisfactory CSA for mandelic acid with DeltaDeltadelta of 24.8?Hz. CSA (S,S)-5 exhibited the best enantiomeric discrimination for alpha-phenyl-alpha-methoxyacetic acid with DeltaDeltadelta 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.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI