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Molecules 2015, 20(11), 20873-20886; doi:10.3390/molecules201119732

Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents

Department of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, P. O. Box 55, FI-00014, Helsinki 00100, Finland
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Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 14 October 2015 / Revised: 3 November 2015 / Accepted: 8 November 2015 / Published: 23 November 2015
(This article belongs to the Section Organic Synthesis)
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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. View Full-Text
Keywords: chiral resolution; chiral solvating agent; (+)-dehydroabietylamine; NMR spectroscopy chiral resolution; chiral solvating agent; (+)-dehydroabietylamine; NMR spectroscopy
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Laaksonen, T.; Heikkinen, S.; Wähälä, K. Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents. Molecules 2015, 20, 20873-20886.

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