Chinese Journal of Catalysis ›› 2014, Vol. 35 ›› Issue (7): 1008-1011.DOI: 10.1016/S1872-2067(14)60080-2

• Communications • Previous Articles     Next Articles

An amphiphilic organic catalyst for the direct asymmetric Michael addition of cycloketone to nitroolefins in water

Jianwei Weia,b, Wengang Guob, Boyu Zhangb, Yan Liub, Xin Dua, Can Lib   

  1. a. Department of Chemistry, Dalian University of Technology, Dalian 116024, Liaoning, China;
    b. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
  • Received:2013-12-21 Revised:2014-03-11 Online:2014-06-28 Published:2014-06-28
  • Supported by:

    This work was supported by the National Natural Science Foundation of China (21002100) and the Fundamental Research Funds for the Central Universities of China (DUT12LK07).

Abstract:

A series of amphiphilic proline-derived mercapto imidazole organic catalysts were synthesized and shown to be very effective with an acid cocatalyst for the asymmetric Michael addition reaction of ketones to nitroolefins with high diastereoselectivity (up to 99:1) and execellent enantioselectivity (up to 96%) using water as solvent.

Key words: Asymmetric catalysis, Emulsion, Organocatalysis, Michael addition