Chinese Journal of Catalysis ›› 2011, Vol. 32 ›› Issue (10): 1573-1576.

• Research Briefing • Previous Articles     Next Articles

Chiral Phosphoric Acid Catalyzed Enantioselective Aza-Michael Addition of Aromatic Amines to Nitroolefins

YANG Lei, XIA Chungu, HUANG Hanmin*   

  1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China
  • Received:2011-07-07 Revised:2011-08-06 Online:2011-09-30 Published:2015-02-12

Abstract: Chiral phosphoric acid was found to be an effective organocatalyst in the enantioselective aza-Michael addition of aromatic amines to nitroolefins giving the corresponding β-nitroamine products in good yields (65%–95%) with moderate to good enantiomeric excesses (16%–70%). This study represents the first example of a chiral phosphoric acid catalyzed asymmetric aza-Michael addition reaction.

Key words: chiral phosphoric acid, aromatic amine, nitroolefin, aza-Michael addition