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- Title
Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents.
- Authors
Laaksonen, Tiina; Heikkinen, Sami; Wähälä, Kristiina
- Abstract
Chiral tertiary and quaternary amine solvating agents for NMR spectroscopy were synthesized from the wood resin derivative (+)-dehydroabietylamine (2). The resolution of enantiomers of model compounds [Mosher's acid (3) and its n-Bu4N salt (4)] (guests) by (+)-dehydroabietyl-N,N-dimethylmethanamine (5) and its ten different ammonium salts (hosts) was studied. The best results with 3 were obtained using 5 while with 4 the best enantiomeric resolution was obtained using (+)-dehydroabietyl-N,N-dimethylmethanaminium bis(trifluoromethane-sulfonimide) (6). The compounds 5 and 6 showed a 1:1 complexation behaviour between the host and guest. The capability of 5 and 6 to recognize the enantiomers of various α-substituted carboxylic acids and their n-Bu4N salts in enantiomeric excess (ee) determinations was demonstrated. A modification of the RES-TOCSY NMR pulse sequence is described, allowing the enhancement of enantiomeric discrimination when the resolution of multiplets is insufficient.
- Subjects
AMINE analysis; CHIRALITY; NUCLEAR magnetic resonance spectroscopy; ENANTIOMERS analysis; AMMONIUM salts; CARBOXYLIC acids; RESOLUTION (Chemistry)
- Publication
Molecules, 2015, Vol 20, Issue 11, p20873
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules201119732