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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (06): 669-672. 上一篇    下一篇

研究论文

手性氨基醇催化的前手性芳酮的不对称还原反应

程青芳*,1，许兴友1，杨绪杰2，尤田耙3   

  1. (1淮海工学院化工系 连云港 222005)
    (2南京理工大学材料化学实验室 南京 210094)
    (3中国科学技术大学化学系 合肥 230026 )
  • 收稿日期:2004-09-23 修回日期:2004-12-14 发布日期:2005-05-30
  • 通讯作者: 程青芳

Enantioselective Borane Reduction of Prochiral Aryl Ketones Catalyzed by Camphyl Aminoalcohols

CHENG Qing-Fang*1, XU Xing-You1, YAN, G Xu-Jie2, YOU Tian-Pa3   

  1. (1 Department of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005)
    (2 Meterials Chemistry Laboratory, Nanjing University of Science and Technol-ogy, Nanjing 210094)
    (3 Department of Chemistry, University of Science and Tech-nology of China, Hefei 230026 )
  • Received:2004-09-23 Revised:2004-12-14 Published:2005-05-30
  • Contact: CHENG Qing-Fang

PDF

2333

被引次数

52

首次以天然D-樟脑的衍生物为原料, 合成了两个新型龙脑基氨基醇配体, 研究了它们与硼烷原位制备成手性噁唑硼烷后, 在不对称催化氢化还原前手性芳酮中的性能, 得到的手性仲醇的对映体过量(ee)值最高可达96%, 还考察了反应温度、时间、溶剂等因素对苯乙酮的不对称氢化还原的化学产率和光学收率的影响.

关键词: 芳酮, 不对称还原, 龙脑基氨基醇, 手性噁唑硼烷

Two camphyl aminoalcohols were synthesized from the ramification of natural D-camphor. The formed chiral oxazaborolidines in situ have been used in the enantioselective borane reduction of prochiral ketones affording the alcohol products with enantiomeric excesses (ee) up to 96%. The effects of reaction temperature, time and solvent on the yield and the enantioselectivity of asymmetric reduction of acetophenone were investigated.

Key words: asymmetric reduction, chiral oxazaborolidine, aryl ketone, camphyl aminoalcohol