Sanzhong Luo,* Xueling Mi, Long Zhang, Song Liu, Hui, Xu, Jin-Pei Cheng*

Between the extremes of transition metal catalysis and biocatalysis, asymmetric organocatalysis has now become the third general approach to the catalytic production of enantiomerically pure organic compounds. Despite the impressive advances in asymmetric organocatalysis in the past few years, the field is still challenged by the low efficiency of organocatalysis. The design and synthesis of novel, efficient and reusable organocatalysts are therefore highly desirable. By ccombining the advantages of organocatalysts and ionic liquids together, the research group of adjunct Prof. Jin-Pei Cheng and assistant Prof. Sanzhong Luo in ICCAS has developed functionalized chiral ionic liquid as a highly efficient and reusable organocatalyst. Their design of that is covalently tethered with an IL moiety, so that the former can serve as a catalytic site and the latter as both the phase tag and chiral induction group. The functionalized CILs function as highly efficient asymmetric organocatalysts for asymmetric Michael addition of ketones and aldehydes to  nitroalkenes with high yields (up to 100%), excellent enantioselectivity (up to 99% ee) and very good diastereoselectivity (syn/anti up to 99:1). The catalyst could be reused for 4 times without loss of stereoselectivities.

Angew. Chem. (2006, 118, 3165);  Angew. Chem. Int. Ed. (2006, 45, 3093).

Figure  Functioned catalyzed Asymmetric Michael reaction (A) and the reusability (B)