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New Chiral Ionic Liquids Based on Enantiopure Sulfate and Sulfonate Anions for Chiral Recognition
Author(s) -
Winkel Andreas,
Wilhelm René
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000801
Subject(s) - chemistry , ionic liquid , enantiopure drug , sulfonate , hydrogen sulfate , metathesis , chiral auxiliary , organic chemistry , inorganic chemistry , enantioselective synthesis , sodium , catalysis , polymerization , polymer
The synthesis of new chiral ionic liquids with chiral anions is described. Chiral sulfate anions were prepared from alcohols of the “chiral pool” in good yields. Subsequent ion metathesis resulted in new salts with tetrabutylphosphonium and 1‐butyl‐3‐methylimidazolium (BMIM) cations. In addition, the synthesis of chiral sulfonate anions from ( R )‐phenylethylamine and formaldehyde–sodium hydrogen sulfate, or sodium vinyl sulfonate is shown, giving new Brønsted basic chiral ionic liquids. The potential of the new ionic liquids as chiral shift reagents was explored. It was possible to use, in addition to Mosher's acid and the Brønsted basic ionic liquids, also 2,2,2‐trifluoro‐1‐phenylethanol with the chiral salts. The neutral alcohol was found to interact with the chiral anions by hydrogen bonding.