Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (01): 8-16. Previous Articles     Next Articles

Review

手性磷酸催化的有机催化不对称反应

高勇军,杨丽华,宋双居,马晶军,唐然肖
边瑞环,刘海燕,吴秋华,王春*   

  1. (河北农业大学理学院 河北省生物无机化学重点实验室 保定 071001)
  • 收稿日期:2006-12-05 修回日期:1900-01-01 发布日期:2008-01-23
  • 通讯作者: 王春

Organocatalytic Asymmetric Reaction Catalyzed byChiral Phosphoric Acids

GAO Yong-Jun, YANG Li-Hua, SONG Shuang-Ju, MA Jing-Jun, TANG Ran-Xiao, BIAN Rui-Huan, LIU Hai-Yan, WU Qiu-Hua, WANG Chun*   

  1. (Hebei Key Laboratory of Bioinorganic Chemistry, College of Sciences, Agricultural University of He-bei, Baoding 071001)
  • Received:2006-12-05 Revised:1900-01-01 Published:2008-01-23
  • Contact: WANG Chun

Chiral phosphoric acids are highly efficient and enantioselective of Brønsted acid organocatalysts discovered very recently. High yields and excellent enantioselectivity were achieved in asymmetric organic reactions involving imines, such as asymmetric Mannich, reductive amination, Pictet-Spengler, aza-Diels-Alder, aza-ene reactions and so on. The presence of the Lewis basic phosphoryl moiety in proximity to the Brønsted acidic proton in chiral phosphoric acids potentially allows for bifunctional catalysis, that is, simultaneous activation of both electrophilic and necleophilic reaction components. The catalyst loading could be lowered to 0.5 mol%. The applications of chiral phosphoric acids in asymmetric organocatalytic reactions are reviewed. The reaction mechanism, catalytic activity and the asymmetric induction influenced by the structure of chiral phosphoric acids and the reaction conditions are also discussed.

Key words: enantioselectivity, asymmetric organocatalysis, chiral phosphoric acid, revi