Cooperative and Enantioselective NbCl<sub>5</sub>/Primary Amine Catalyzed Biginelli Reaction

Yongfeng Cai, Huameng Yang, Li Li, Kezhi Jiang, Guoqiao Lai, Jianxiong Jiang, Li‐Wen Xu

European Journal of Organic Chemistry · 2010 · 62 citations · 39 references

Concepts

Abstract

Abstract A series of chiral organocatalysts and Lewis acids have been evaluated in the Lewis acid/organocatalysts‐based cooperative catalytic Biginelli reaction, which resulted in the determination of a novel cooperative Lewis acid/primary amine catalyst system, NbCl 5 /QN‐NH 2 . The synergistic effect of NbCl 5 and the quinine‐derived primary amine is pronounced and gave dihydropyrimidiones (DHPMs) in moderate to good enantioselectivities (up to 84 % ee ) and good to excellent yields (up to 99 % yield) under mild conditions.

References

39