Dr. Hui Wu’s team published their most recent discovery in Chemical and Engineering Journal


Rui Yuan, Yuan-jiang Wang, Yue Fang, Wen-hui Ge, Wei  Lin, Ming-qi Li, Jiang-biao Xu, Yu Wan, Yun Liu, Hui Wu*, The First Direct  Synthesis of Chiral Tröger's Bases Catalyzed by Chiral Glucose-containing  Pyridinium Ionic Liquids, Chem. Eng. J. 316, 1026, 2017.

Ab s t r a c t:Tröger’s base (TB) and its derivatives, especially  chiral TBs are widely used in many fields. Although there is an urgent demand  for the direct synthesis of pure enantiomers of TBs, convenient synthetic  strategies are far less developed. Ionic liquids are green and recyclable  solvent, therefore, in this paper, novel chiral glucose-containing pyridinium  ionic liquids (1-((2S,3S,4R,5S,6S)-3,4,5-triacetoxy-6-(acetoxymethyl)tetra  hydro-2H-pyran-2-yl)pyridin-1-ium tetrafluoroborate, [Py-G]+[BF4]-)  was synthesized and used as catalyst and solvent, while trifluoroacetic acid  (TFA) was used as co-catalyst, to promote the one-step direct asymmetric  synthesis of Tröger’s bases with pyrazol flank firstly at room temperature  with high yields (up to 83%) and high ee value (up to 84%). A reasonable  reaction mechanism was investigated by using chemical experiments, 1H  NMR analysis and mass spectrometry. The novel method is environmental  friendly and the result indicated its value of practical application.


1.Novel chiral glucose-containing pyridinium ionic  liquids were synthesized.

2.The new chiral ionic liquids were used as catalyst  and solvent.

3.The direct asymmetric synthesis of Tröger’s base  derivatives was put forward firstly.

4.The reasonable reaction mechanism was carefully  investigated.

5.The strategy is green, cost-effective,  operationally convenient and highly efficient.

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