高等学校化学学报

高等学校化学学报 ›› 2002, Vol. 23 ›› Issue (7): 1318.

• 研究简报 • 上一篇    下一篇

手性氨基二醇的合成及其在二乙基锌对醛不对称加成反应中的应用

徐前永, 武同兴, 潘鑫复   

  1. 兰州大学化学系, 应用有机化学国家重点实验室, 兰州 730000
  • 收稿日期:2001-04-24 出版日期:2002-07-24 发布日期:2002-07-24
  • 通讯作者: 潘鑫复(1937年出生),男,教授,博士生导师.从事不对称合成研究.E-mail:panxf@lzu.edu.cn. E-mail:panxf@lzu.edu.cn.
  • 基金资助:

    国家自然科学基金(批准号:20172023)

Preparation of Chiral Aminodiols and Their Applications in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes

XU Qian-Yong, WU Tong-Xing, PAN Xin-Fu   

  1. Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, China
  • Received:2001-04-24 Online:2002-07-24 Published:2002-07-24

PDF (PC)

被引次数

6

关键词: 不对称加成反应, 二乙基锌, 手性氨基二醇

Abstract: Four new chiral aminodiols 1-4, which were prepared from methyl L-proline in 2 steps, were applied in the enantioselective addition of diethylzinc to benzaldehyde. The results indicated that the enantioselectivities enhance with increasing the bulkiness of substituents on chiral ligands and with chiral ligand 4 giving the best result. When ligand 4 was used to catalyze the enantioselective addition of diethylzinc to aromatic aldehydes, the substituents affect the enantioselectivities slightly and 1-naphthaldehyde gives the best enantiomeric excess(up to 75.3% ). On the other hand, 4-(dimethylamino)benzaldehyde gives a low enantiomeric excess, which may most likely arise from a non steroselective ethyl transfer to aldehyde promoted by zinc coordination of amino group. For aliphatic aldehydes, poor enantiomeric excesses are generally given.

Key words: Enantioselective addition, Diethylzinc, Chiral aminodiol

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