Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (04): 486-498. Previous Articles     Next Articles

Reviews

手性磷酸在不对称反应中的应用

苏亚军,史福强   

  1. (贵州大学精细化工研究开发中心 教育部绿色农药与农业生物工程重点实验室 贵阳 550025)
  • 收稿日期:2009-04-28 修回日期:2009-08-28 发布日期:2010-04-28
  • 通讯作者: 史福强 E-mail:fcc.fqshi@gzu.edu.cn
  • 基金资助:

    国家级.国家自然科学基金

Applications of Chiral Phosphoric Acid to Asymmetric Reactions

Su Yajun Shi Fuqiang   

  1. (Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025)
  • Received:2009-04-28 Revised:2009-08-28 Published:2010-04-28
  • Contact: Shi Fu-Qiang E-mail:fcc.fqshi@gzu.edu.cn

Chiral phosphoric acid has received increasing attention as a highly efficient and enantioselective catalyst. Chiral phosphoric acid with 1,1 -binaphthyl (BINOL) unit has been applied to asymmetric transfer hydrogenation of imines, enantioselective Friedel-Crafts reaction, and asymmetric Mannich reaction etc. Chiral phosphoric acid can act as both proton donor and proton acceptor simultaneously, therefore, it is able to activate both substrates. Both hindrance and pKa of chiral phosphoric acid with BINOL unit can be adjusted by changing the 3,3 -substituents. So the enantioselectivity of chiral phosphoric acid can be modified. More investigations, especially in computational chemistry, on the reaction mechanism catalyzed by chiral phosphoric acid have been carried out to design new chiral phosphoric acid and extend its applications. The applications of chiral phosphoric acid to asymmetric reactions are reviewed, involving the latest computational results.

Key words: Chiral phosphoric acid, asymmetric reaction, enantioselectivity, reaction mechanism