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2023 , Vol. 43 >Issue 3: 855 - 872

DOI: https://doi.org/10.6023/cjoc202212039

综述与进展

多取代烯烃的Z∶E高选择性合成制备

  • 郭萍 ,
  • 周勇 ,
  • 赵杰
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  • 华东理工大学化学与分子工程学院 上海 200237

收稿日期: 2022-12-03

  修回日期: 2023-02-25

  网络出版日期: 2023-03-01

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Z∶E Selective Preparation of Disubstituted Internal Alkenes and Trisubstituted Alkenes

  • Ping Guo ,
  • Yong Zhou ,
  • Jie Zhao
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  • School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237
* Corresponding author. E-mail:

Received date: 2022-12-03

  Revised date: 2023-02-25

  Online published: 2023-03-01

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摘要

烯烃是工业生产和药物合成中最常见的原料之一, 关于烯烃制备方法的报道层出不穷. 由于Z-构型烯烃与E-构型烯烃在理化性质和生物活性等方面存在很大的差异, 所以烯烃结构的Z∶E构型控制是合成方法学的热点之一. 综述了烯烃的立体选择性合成方法, 着重总结了双取代内烯烃和三取代烯烃的Z∶E构型的选择性制备. 以Z∶E选择性为主要分类标准, 解读了Wittig反应、取代烷烃消除反应、烯烃异构化反应、烯烃复分解反应、烯烃偶联反应、炔烃加成反应的相关报道, 并比较详细地描述了这些合成方法中的催化剂种类和Z∶E选择性的控制因素.

关键词： 双取代内烯烃; 三取代烯烃; Z∶E选择性

本文引用格式

郭萍 , 周勇 , 赵杰 . 多取代烯烃的Z∶E高选择性合成制备[J]. 有机化学, 2023 , 43(3) : 855 -872 . DOI: 10.6023/cjoc202212039

Abstract

Olefin is one of the most important bulk chemicals in industry as well as commonly used starting materials in pharmaceutical field. Since Z-olefins and E-olefins exhibit great differences in physicochemical properties and biological activities, the Z∶E configuration control has been playing important roles in olefin preparation. The selective synthetic methods of Z∶E configurations of disubstituted inner alkenes and trisubstituted alkenes are reviewed, including the Wittig reaction, substituted alkane elimination reaction, olefin isomerization reaction, olefin metathesis, olefin coupling reaction, and alkyne addition reaction. The catalyst types and controlling factors of Z∶E selectivity in these synthetic examples are described in detail.

Key words： disubstituted internal olefins; trisubstituted olefins; Z∶E selectivity

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