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

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

Volume: 9 Issue: 1

Author(s): Thi-Kim-Thu Truong, Olivier Nguyen Van Buu, Audrey Aupoix, Bruce Pegot and Giang Vo-Thanh

Affiliation:

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

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.

Cite this article as:

Truong Thi-Kim-Thu, Nguyen Van Buu Olivier, Aupoix Audrey, Pegot Bruce and Vo-Thanh Giang, Chiral Ionic Liquids Derived from (-)-Ephedrine and Carbohydrates: Synthesis,Properties and Applications to Asymmetric Synthesis and Catalysis, Current Organic Synthesis 2012; 9 (1) . https://dx.doi.org/10.2174/157017912798889143