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有机化学
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有机化学 ›› 1997, Vol. 17 ›› Issue (1): 87-91. 上一篇    下一篇

研究论文

光学活性N-N-二烷基-β-氨基醇硼烷配合物对酮肟醚的不对称还原反应(Ⅱ)

赵军;王亚东;杨世琰;金道森;魏学红   

  1. 浙江工业大学化学工程学院;中国科学院兰州化学物理研究所;山西大学化学系
  • 发布日期:1997-02-25

Asymmetric reduction of ketoxime ethers using optically active N,N-dialkyl-β-aminoalcohol-borane complexes (Ⅱ)

ZHAO JUN;WANG YADONG;YANG SHIYAN;JIN DAOSEN;WEI XUEHONG   

  • Published:1997-02-25

光学活性(S)-(-)-2-(1-吡咯烷基)-1,1-二苯基-丙醇-1(1a)和(S)-(-)-2(1-吡咯烷基)-1,1,3-三苯基-丙醇-1(1b), 分别与过量的硼烷反应, 生成相应的硼烷-手性翁唑硼烷配合物, 可用于脂肪酮肟醚和芳香酮肟醚的碳-氮双键的不对称还原反应, 得到光学活性伯胺, 化学收率则为52~76%, 光学收率为6~99%, 讨论了不同还原底物的结构对立体选择性的影响作用。

关键词: 光学活性, 硼烷, 苯 P, 翁唑硼烷, 酮肟醚, 丙醇 P, 立体选择性, 不对称, 还原反应, 吡咯 P

The borane-chiral oxazoborolidine complexes were prepared from (S)-(-)-2-(1-pyrrolidino)-1,1-diphenylpropan-1-ol (1a) and (S)-(-)-2- (1-pyrrolidino)-1,1,3-triphenylpropan-1-ol (1b) with borane in THF, respectively. These reagents were used in asymmetric reduction of C=N double bonds of aliphatic and aromatic ketoxime ethers to yield chiral primary amines, which are (S)-configuration in most of the cases, with chemical yields (52~76%) and optical yields (6~99%). The effects of the structures of substrates and enantioselectivity were also discussed.

Key words: STEREOSELECTIVITY, BORANE, PROPANOL P, ASYMMETRY, REDUCTION REACTION, PYRROLE P, BENZENE P

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