Synthesis and applications of secondary amine derivatives of (+)-dehydroabietylamine in chiral molecular recognition

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Laaksonen , T , Heikkinen , S & Wähälä , K 2015 , ' Synthesis and applications of secondary amine derivatives of (+)-dehydroabietylamine in chiral molecular recognition ' Organic & Biomolecular Chemistry , vol. 13 , no. 42 , pp. 10548-10555 . DOI: 10.1039/c5ob01667c

Title: Synthesis and applications of secondary amine derivatives of (+)-dehydroabietylamine in chiral molecular recognition
Author: Laaksonen, Tiina; Heikkinen, Sami; Wähälä, Kristiina
Contributor: University of Helsinki, Synthesis and Analysis
University of Helsinki, Department of Chemistry
University of Helsinki, Kristiina Wähälä-Hase / Principal Investigator
Date: 2015
Language: eng
Number of pages: 8
Belongs to series: Organic & Biomolecular Chemistry
ISSN: 1477-0520
URI: http://hdl.handle.net/10138/224649
Abstract: (+)-Dehydroabietylamine (1a), the novel derivatives (2a-6a) and their NTf2 salts (1b-6b) were tested as chiral NMR solvating agents for the resolution of enantiomers of the model compound Mosher's acid (7) and its n-Bu4N salt (8). Best enantiomeric discrimination of 7 was obtained using bisdehydroabietyl-amino-N-1, N-2-ethane-1,2-diamine (6a), and of 8 using N-(dehydroabietyl)-2-(dehydroabietylamino) ethanaminium bis((trifluoromethyl)-sulfonyl)-amide (6b). For the maximal resolution of enantiomers of 8, 1.0 eq. of 6b were needed. However, 0.5 eq. of 6a sufficed for the maximal resolution of enantiomers of 7. Enantiomeric excess studies were successfully conducted using 6a and 6b. The capability of 6a and 6b to recognize the enantiomers of various a-substituted carboxylic acids and their n-Bu4N salts were examined. Best resolutions were observed for aliphatic and aromatic carboxylic acids bearing an electronegative alpha-substituent. Now the ee studies on such non-aromatic carboxylic acids are also feasible.
Subject: SOLVATING AGENTS
CARBOXYLIC-ACIDS
IONIC LIQUIDS
NMR ENANTIODISCRIMINATION
ENANTIOMERIC EXCESS
DISCRIMINATION
PURE
RESOLUTION
H-1-NMR
116 Chemical sciences
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