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有机化学
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有机化学 ›› 1998, Vol. 18 ›› Issue (2): 142-145. 上一篇    下一篇

研究论文

一类新型的双β-氨基醇的合成及催化硼烷对芳酮的不对称还原反应

黎星术;谢如刚   

  1. 四川联合大学化学系
  • 发布日期:1998-04-25

Preparation of chiral bis-β-amino alcohols and their application in the enantioselective catalytic borane reduction of aromatic ketones

LI XINGSHU;XIE RUGANG   

  • Published:1998-04-25

被引次数

13

以L-半胱氨酸盐酸盐出发，经与二卤代烷偶联，成酯和格氏反应制得三种双手性β-氨基醇，1,2-双[R-2-氨基-3-羟基-3,3-二苯基丙硫基]乙烷(4a)，1,3-双[R-2-氨基-3-羟基-3,3-二苯基丙硫基]丙烷(4b)，1,4-双[R-2-氨基-3-羟基-3,3-二苯基丙硫基]丁烷(4c)。将此类双手性β-氨基醇与硼烷在THF溶液中反应，in situ制备双手性恶唑硼烷催化硼烷对芳酮的不对称还原，产物苯乙醇的光学收率达72.8%、α-溴代苯乙醇的光学收率达91.4%。

关键词: 催化反应, 手征性, 氨基醇 P, 恶唑酮 P, 催化剂, 酮 P, 硼烷, 硼烷类, 芳香族化合物, 还原反应

Three new chiral bis-β-amino alcohols, 1,2-bis[R-2-amino- 3-hydroxyl-3,3-diphenyl propylthio]ethane (4a), 1,3-bis[R-2-amino- 3-hydroxyl-3,3-diphenyl propylthio]propane (4b), 1,4-bis[R-2-amino- 3-hydroxyl-3,3-diphenyl propylthio]butane (4c), were synthesized starting with L-cysteine. Their application in the enantioselective catalytic borane reduction of aromatic ketones were studied and the enantiomeric excess 72.8% for acetophenone and 91.4% for α-bromo acetophenone have been gained.

Key words: CATALYTIC REACTION, AMINO ALCOHOL P, CHIRALITY, BORANES, BORANE, KETONE P, REDUCTION REACTION, AROMATIC COMPOUNDS, CATALYST

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