中华医学超声杂志

应用化学 ›› 1994, Vol. 0 ›› Issue (2): 70-72.

• 研究论文 • 上一篇    下一篇

手性铜催化剂的制备及在环丙烷羧酸酯不对称合成中的应用

杨智才, 张小微, 陈良   

  1. 华东师范大学化学系 上海 200062
  • 收稿日期:1993-03-02 修回日期:1993-10-20 出版日期:1994-04-10 发布日期:1994-04-10
  • 基金资助:
    国家自然科学基金资助课题

Chiral Copper Complexes for Asymmetric Synthesis of Cyclopropanecarboxylic Esters

Yang Zhicai, Zhang Xiaowei, Chen Liang   

  1. Department of Chemistry, East China Normal University, Shanghai 200062
  • Received:1993-03-02 Revised:1993-10-20 Published:1994-04-10 Online:1994-04-10

PDF

381

被引次数

3 | 1

摘要： 3类手性配体d-10-樟脑磺酸及其衍生物,α-(-)-羟蒎酮及其衍生物,双唑啉衍生物分别与铜(Ⅱ)形成手性铜配合物,催化重氮乙酸酯与1,1-二苯乙烯或异丁烯的环丙烷化加成反应,得到光学活性环丙烷羧酸酯,不对称诱导最高可达95%e.e。

关键词: 重氮乙酸酯, 二苯乙烯, 异丁烯, 环丙烷化, 樟脑磺酸, 羟蒎酮, 双唑啉, 手性铜催化剂

Abstract: Three kinds of optically active ligands were combined with copper(Ⅰ)-acetate to give 8 chiral copper complexes:d-camphor-10-sulfonic acid and its derivatives of Schiff base, hydroxypinocamphone and its derivatives of Schiff base,and bis-oxazoline. The optical yields of 2,2-diphenylcyclopropanecarboxylic ethyl ester were 5%～50e.e.. The reaction of diphenylethylene or isobutylene with menthyl diazoaceteta by chiral copper(Ⅰ) bis-oxazo-line gave an enantioselectivity of 81.5%e.e. and 95%e.e., respectively.

Key words: diazoacetate, diphenyl ethylene, isobutylene, cyclopropanation, camphorsulfonicacid, hydroxypinocamphone, bisoxazoline, chiral copper complex

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