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CBS催化硼烷胺配合物不对称还原法制备(S)-3-氯-1-苯基-1-丙醇

白灵,肖鸽,卓广澜*   

  1. (浙江理工大学化学系 杭州 310018)
  • 收稿日期:2011-10-08 修回日期:2012-01-19 出版日期:2012-09-10 发布日期:2012-09-10
  • 通讯作者: 卓广澜,副教授; Tel:0571-86843082; Fax:0571-89189769; E-mail:zhuoguanglan@163.com; 研究方向:催化化学,药物与中间体合成

Asymmetric Synthesis of (S)-3-Chloro-1-phenyl-1-propanol Using Borane Amine Complex-CBS as Catalyst

BAI Ling , XIAO Ge, ZHUO Guanglan*   

  1. (Department of Chemistry,Zhejiang Science-Technique University,Hangzhou 310018,China)
  • Received:2011-10-08 Revised:2012-01-19 Published:2012-09-10 Online:2012-09-10
  • Contact: zhuo

摘要: 分别以R-α,α-二苯基脯氨醇、(1R,2S)-2-氨基-1,2-二苯基乙醇和(1R,2S)-(-)-1-氨基-2-茚醇为催化剂,以多种硼烷胺配合物为还原剂,由β-氯代苯乙酮不对称合成(S)-3-氯-1-苯基-1-丙醇,收率88.3%~93.8%,e.e.值为81.6%~87.7%。 用硼烷胺配合物代替硼烷-THF和硼烷二甲硫醚,稳定性好,容易计量和安全操作。

关键词: 硼烷胺配合物, CBS催化, (S)-氯苯基丙醇, 氟西汀

Abstract: (S)-3-Chloro-1-phenyl-1-propanol was synthesized asymmetrically by using catalysts (R)-α,α-diphenyl-2-pyrrolidinemethanol, (1R,2S)-2-amino-1,2-diphenylethanol and (1R,2R)-1-amino-2-indanol with amine borane complexes, with a yield of 88.3%~93.8%, ee% 81.6~87.7. These amine borane complexes are more stable and safe than the borane-tetrahydrofuran complex and borane-methyl sulfide complex.

Key words: borane amine complex, CBS catalyst, (S)-chlorophenylpropanol, Fluoxetine

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