Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (04): 518-522. Previous Articles     Next Articles

Original Articles

手性β-氨基醇的合成及其催化二乙基锌与醛的不对称加成反应

柳文敏,王平安,张生勇*,姜茹   

  1. (第四军医大学药学系化学教研室 西安 710032)
  • 收稿日期:2005-09-29 修回日期:2006-01-26 发布日期:2006-03-31
  • 通讯作者: 张生勇

Synthesis of Chiral β-Aminoalcohol and Its Catalysis in the Asymmetric Addition of Diethylzinc to Aldehyde

LIU Wen-Min,WANG Pin-An,ZHANG Sheng-Yong*,JIANG Ru   

  1. (Department of Chemistry, School of Pharmacy, The Fourth Military Medical University of
    The Peoples Liberation Army, Xi'an 710032)
  • Received:2005-09-29 Revised:2006-01-26 Published:2006-03-31
  • Contact: ZHANG Sheng-Yong

Seven chiral β-aminoalcohols were synthesized by Sharpless asymmetric dihydroxylation and used as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes.The effects of the amount and the structure of catalysts, solvent and reaction temperature on enantioselectivity were also studied. When the amount of catalyst was 5 mol% relative to aldehyde, solvent was toluene and reaction temperature was -10 ℃, the chiral ligand, 1S,2R-(+)-2-amino-1,2-diphenylethanol (1b), efficiently catalyzed the asymmetric addition of diethylzinc to aldehydes with the yield up to 100% and enantiomeric excess up to 85%.

Key words: chiral β-aminoalcohol, catalysis, diethylzinc, asymmetric addition