Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2912-2919.DOI: 10.6023/cjoc201902026 Previous Articles     Next Articles




  1. 济宁学院化学与化工系 山东曲阜 273155
  • 收稿日期:2019-02-24 修回日期:2019-03-29 发布日期:2019-05-21
  • 通讯作者: 郭庆君

Asymmetric Synthesis of Diarylmethanols by Chiral Phosphoramide Ligands Catalysts

Guo, Qingjun*()   

  1. Key Laboratory of Inorganic Chemistry in Universities of Shandong, Department of Chemistry and Chemical Engineering, Jining University, Qufu 273155, Shandong
  • Received:2019-02-24 Revised:2019-03-29 Published:2019-05-21
  • Contact: Guo, Qingjun

In order to improve the application of chiral phosphoramide ligands in catalytic asymmetric reactions, thiophosphoramide, which was synthesized from trans-1,2-cyclohexanediamine was used as a catalyst to synthesize chiral diarylmethanol compounds through addition reaction. The catalytic activity of the ligand in the asymmetric addition reaction of the arylalkyl zincs to the aromatic aldehyde can be as high as 94% ee under the optimized reaction conditions in the presence of 30 mol% phosphoramide ligand N-((1R,2R)-2-(isopropylamino)cyclohexyl)-P,P-diphenylphosphinic amide (9c) and the corresponding chiral diarylmethanol compound was obtained with the yields of >90%. Despite the large amount of catalyst, the ligand is very convenient to recycle and reuse in this system. At the same time, the reaction mechanism was speculated, and it is believed that the quaternary transition state and the six-element transition state formed by the reaction process are beneficial to improve the enantioselectivity of the reaction.

Key words: chiral thiophosphoramide ligand, diarylmethanols, asymmetric catalysis