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Chiral Imidazolium Ionic Liquids Derived from ( S )‐Prolinamine as Organocatalysts in the Asymmetric Michael Reaction and Michael‐Aldol Cascade Reaction under Solvent‐Free Conditions
Author(s) -
ObregónZúñiga Arturo,
GuerreroRobles Marco,
Juaristi Eusebio
Publication year - 2017
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.201700133
Subject(s) - cyclohexanone , aldol reaction , chemistry , michael reaction , ionic liquid , enantioselective synthesis , organocatalysis , stereoselectivity , organic chemistry , solvent , nitroaldol reaction , catalysis , cascade , combinatorial chemistry , chromatography
The synthesis of three new chiral imidazolium ionic liquids (prepared by the combination of one new chiral organic cation with different anions) and their application in the enantioselective Michael reaction between cyclohexanone and substituted nitrostyrenes under solvent‐free conditions is described. In addition, the first asymmetric cascade Michael‐aldol reaction of cyclohexanone and benzylidenepyruvate organocatalyzed by chiral ionic liquids is reported. Recyclability of the catalyst was evaluated for both reactions, and no loss in stereoselectivity up to the third cycle was observed.