Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents
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...
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| Format: | Article |
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MDPI AG
2015-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/11/19732 |
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| author | Tiina Laaksonen Sami Heikkinen Kristiina Wähälä |
| author_facet | Tiina Laaksonen Sami Heikkinen Kristiina Wähälä |
| author_sort | Tiina Laaksonen |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-11T16:33:02Z |
| format | Article |
| id | doaj.art-37aedca4519744eea6ab08b8a8ce2b52 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T16:33:02Z |
| publishDate | 2015-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-37aedca4519744eea6ab08b8a8ce2b522022-12-22T00:58:32ZengMDPI AGMolecules1420-30492015-11-012011208732088610.3390/molecules201119732molecules201119732Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating AgentsTiina Laaksonen0Sami Heikkinen1Kristiina Wähälä2Department of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, P. O. Box 55, FI-00014, Helsinki 00100, FinlandDepartment of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, P. O. Box 55, FI-00014, Helsinki 00100, FinlandDepartment of Chemistry, University of Helsinki, A.I. Virtasen aukio 1, P. O. Box 55, FI-00014, Helsinki 00100, FinlandChiral 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.http://www.mdpi.com/1420-3049/20/11/19732chiral resolutionchiral solvating agent(+)-dehydroabietylamineNMR spectroscopy |
| spellingShingle | Tiina Laaksonen Sami Heikkinen Kristiina Wähälä Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents Molecules chiral resolution chiral solvating agent (+)-dehydroabietylamine NMR spectroscopy |
| title | Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents |
| title_full | Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents |
| title_fullStr | Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents |
| title_full_unstemmed | Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents |
| title_short | Synthesis of Tertiary and Quaternary Amine Derivatives from Wood Resin as Chiral NMR Solvating Agents |
| title_sort | synthesis of tertiary and quaternary amine derivatives from wood resin as chiral nmr solvating agents |
| topic | chiral resolution chiral solvating agent (+)-dehydroabietylamine NMR spectroscopy |
| url | http://www.mdpi.com/1420-3049/20/11/19732 |
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