高等学校化学学报

高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (9): 1391.

• 论文 • 上一篇    下一篇

TiCl4-Mg介导的立体选择性的频哪醇偶联反应研究

厉廷有1, 王丽萍1, 张涛1, 李耀先2, 王宗睦1   

  1. 1. 吉林大学生命科学学院;
    2. 吉林大学化学系, 长春 130023
  • 收稿日期:1999-12-30 出版日期:2000-09-24 发布日期:2000-09-24
  • 通讯作者: 王宗睦(1934年出生),男,教授,博士生导师,主要从事生物有机和有机合成方法学研究.

Studies on the Stereoselectivity of Pinacol Coupling Reaction Mediated by TiCl4-Mg

LI Ting-You1, WANG Li-Ping1, ZHANG Tao1, LI Yao-Xian2, WANG Zong-Mu1   

  1. 1. College of Life Science;
    2. Department of Chemistry, Jilin University, Changchun 130021, China
  • Received:1999-12-30 Online:2000-09-24 Published:2000-09-24

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摘要： 以TiCl4-Mg和TiCl4-Mg-TMEDA为偶联剂实现对芳香醛高非对映选择性的还原偶联反应.以3种类型的手性试剂对TiCl4-Mg系统进行修饰,对苯甲醛的反应最高可得到50%对映体过量的偶联产物.

关键词: 频哪醇偶联反应, 芳香醛, 四氯化钛-镁, 立体选择性, 对映选择性

Abstract: TiCl4-Mg and TiCl4-Mg-TMEDAsystems are used as reagents of pinacol coupling reaction, thus reductive coupling of aromatic aldehydes with a high stereoselectivity. The observed stereochemistry of the reaction is briefly discussed in term of Ti-bridging controlled models. Three kinds of chiral auxiliary 1,4-diamines, 1,4-diphosphines and 1,4-diethers, are used in the pinacol formation reaction of benzaldehyde mediated by TiCl4-Mg, and hydrobenzoin was obtained with ee 50% of (R,R)-isomer. when N,N,N',N'-tetramethyl-2,3-O-isopropylidene-2,3-dihydroxy, 1,4-butanediamine was used as chiral modifier.

Key words: Pinacol coupling reaction, Aromatic aldehydes, Titanium tetrachloride-magnesium, Stereoselectivity, Enantioselectivity

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