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Chiral Ionic Liquids Derived from (-)-Ephedrine and Carbohydrates: Synthesis,Properties and Applications to Asymmetric Synthesis and Catalysis

[ Vol. 9 , Issue. 1 ]

Author(s):

Thi-Kim-Thu Truong, Olivier Nguyen Van Buu, Audrey Aupoix, Bruce Pegot and Giang Vo-Thanh   Pages 53 - 64 ( 12 )

Abstract:


A novel class of chiral ammonium and imidazolium-based ionic liquids containing a chiral moiety and a free hydroxyl function has been designed and synthesized using (-)-ephedrine, isosorbide and isosmannide as naturally chiral sources. Some physical properties of these salts such as melting point, glass-transition temperature, thermal degradation, chemical stability and specific rotation have been characterized. These chiral ionic liquids were found to catalyze the asymmetric Baylis-Hillman reaction, aza Diels-Alder reaction and Michael addition giving good yields and moderate stereoselectivities. Chiral ionic liquids are recycled while their efficiency is preserved.

Keywords:

Asymmetric aza Diels-Alder reaction, Asymmetric Baylis-Hillman reaction, Ephedrine, Chiral ionic liquids, Isomannide, isosorbide, Michael addition, Microwave-activation, conventional organic solvents, incombustibility, racemates

Affiliation:

Laboratoire de Catalyse Moleculaire,Institut de Chimie Moleculaire et des Materiaux d'Orsay, CNRS-UMR 8182,Universite Paris-Sud 11, 91405 Orsay Cedex, France.



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