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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1816-1819. 上一篇    下一篇

研究简报

选择性合成手性八氢NOBIN和四氢NOBIN

李新生*,a,b ; 孟祥燕b ; 徐东成a,b   

  1. (a浙江师范大学物理化学研究所 浙江省固体表面反应化学重点实验室 金华 321004)
    (b浙江师范大学化学系 金华 321004)
  • 收稿日期:2008-03-02 修回日期:2008-04-17 发布日期:2008-10-20
  • 通讯作者: 李新生

Selective Synthesis of Chiral Octahydro-NOBIN and Tetrahydro-NOBIN

LI, Xin-Sheng*,a,b ; MENG, Xiang-Yanb; XU, Dong-Cheng a,b   

  1. (a Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry,
    Zhejiang Normal University, Jinhua 321004)
    (b Department of Chemistry, Zhejiang Normal University, Jinhua 321004)
  • Received:2008-03-02 Revised:2008-04-17 Published:2008-10-20
  • Contact: LI, Xin-Sheng

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通过部分氢化手性的(S)-NOBIN [(S)-2-氨基-2’-羟基-1,1’-联萘]选择性地合成了(S)-H8-NOBIN和(S)- -NOBIN. 弱极性溶剂(环己烷)和强极性溶剂(2,2,2-三氟乙醇和含乙酸的乙醇)几乎专一地得到(S)-H8-NOBIN (92%). 而中等极性溶剂(甲醇, 乙醇和异丙醇)以中等产率得到(S)- -NOBIN (66%).

关键词: 氢化, 5’,6’,7’,8’-四氢-2-氨基-2’-羟基-1,1’-联萘, 催化剂, 2-氨基-2’-羟基-1,1’-联萘, 手性

(S)- -NOBIN [(S)- -(S)-2-amino-2’-hydroxy-1,1’-binaphthyl] and (S)-H8-NOBIN were obtained by se-lective partial hydrogenation of the corresponding (S)-NOBIN. Weak-polar (cyclohexane) and strong polar solvent (2,2,2-trifluoroethanol and AcOH/EtOH) of the reaction system led to (S)-H8-NOBIN as the main product (up to 92% yield). Moderate polar solvent (methanol, ethanol or iso-propanol) of the reaction system provided (S)- -NOBIN as the main product (up to 66% yield).

Key words: catalyst, hydrogenation, chirality, 5’,6’,7’,8’-tetrahydro-2- amino-2’-hydroxy-1,1’-binaphthyl, 2-amino-2’-hydroxy-1,1’-binaphthyl