Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles     Next Articles

Application of Aziridino Alcohols as Chiral Ligands in Zinc-catalyzed Enantioselective Henry Reaction

WANG Xiaojuan1, LI Gaowei1, WANG Mincan2*, GUO Rui2, LIU Lantao1, ZHAO Wenxian1*   

  1. (1.School of Chemistry and Chemical Engineering and Key Laboratory of New
    Organic Materials Synthesis,Shangqiu Normal University,Shangqiu 476000,China;
    2.Department of Chemistry,Zhengzhou University,Zhengzhou 450052,China)
  • Received:2013-01-31 Revised:2013-03-13 Published:2014-01-10 Online:2014-01-10
  • Contact: xiaojuan wang

Abstract: A pair of diastereoisomeric aziridino alcohols which could be readily prepared from the reaction between (S)-α-methylbenzyl amine and methyl acrylate has been used as chiral ligands in zinc-catalyzed enantioselective Henry reaction between nitromethane and arylaldehydes. A moderate enantioselectivity of β-nitroalcohol, up to 64% ee value, could be achieved in this catalytic reaction. The possible transition states of the reaction were proposed.

Key words: Henry reaction, zinc catalyst, aziridino alcohol ligand

CLC Number: