1-Ethyl-3-methylimidazolium tartrate chiral ionic liquids: preparation, characterization and opportunities thereof

A unified acid/base synthetic access to tartrate-based chiral ionic liquids relying on the generation of cation hydroxide salts with AgOH was challenged with the preparation of sensitive 1-ethyl-3-methylimidazolium derivatives. Systematic variation of the starting tartaric acid stoichiometry and con...

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Bibliographic Details
Published inNew journal of chemistry Vol. 42; no. 23; pp. 18739 - 18748
Main Authors Castellan, Tessa, Cuyamendous, Claire, Fitremann, Juliette, Galano, Jean-Marie, Oger, Camille, Durand, Thierry, Guillen, Frédéric, Génisson, Yves
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 2018
Royal Society of Chemistry [1987-....]
Subjects
Chemical Sciences
Configurations
Ionic liquids
Ions
Metabolites
NMR
Nuclear magnetic resonance
Solvents
Stoichiometry
Tartaric acid
Viscosity
Viscosity measurement
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Summary:A unified acid/base synthetic access to tartrate-based chiral ionic liquids relying on the generation of cation hydroxide salts with AgOH was challenged with the preparation of sensitive 1-ethyl-3-methylimidazolium derivatives. Systematic variation of the starting tartaric acid stoichiometry and configuration led to eight stereoisomeric 1-ethyl-3-methylimidazolium hydrogen tartrate or di-(1-ethyl-3-methylimidazolium)tartrate entities. These salts were all characterised as proper ionic liquids. An unprecedented influence of the configuration ((2 S ,3 S ), or (2 R ,3 R ) vs. racemic or meso ) on dynamic viscosity was observed. The relevance of such tartrate salts as task-specific ionic liquids was demonstrated in a synthetically useful base-promoted intramolecular cyclisation of a C 2 -symmetrical bis-epoxide en route to the total synthesis of phytofuran metabolites.
ISSN:1144-0546
1369-9261
DOI:10.1039/C8NJ03175D