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




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Department of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, P. O. Box 55, FI-00014, Helsinki 00100, Finland





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Academic Editor: Jean Jacques Vanden Eynde

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 bistrifluoromethane-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





Author: Tiina Laaksonen, Sami Heikkinen and Kristiina Wähälä *

Source: http://mdpi.com/



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