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2021 , Vol. 41 >Issue 11: 4467 - 4475

DOI: https://doi.org/10.6023/cjoc202105002

研究论文

氮杂环卡宾催化乙酸酯和β-硅基烯酮的[4+2]环合反应:高立体选择性合成β-硅基δ-内酯

  • 张雨霞 ,
  • 郭京程 ,
  • 黄杰 ,
  • 付振乾
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  • a 南京工业大学先进材料研究院 南京 211816
    b 南京工业大学化学与分子工程学院 南京 211816

收稿日期: 2021-05-01

  修回日期: 2021-07-05

  网络出版日期: 2021-07-26

基金资助

国家自然科学基金(21602105)

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N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones

  • Yuxia Zhang ,
  • Jingcheng Guo ,
  • Jie Huang ,
  • Zhenqian Fu
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  • a Institute of Advanced Materials, Nanjing Tech University, Nanjing 211816
    b School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816
* Corresponding authors. E-mail: ;

Received date: 2021-05-01

  Revised date: 2021-07-05

  Online published: 2021-07-26

Supported by

National Natural Science Foundation of China(21602105)

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摘要

在氮杂环卡宾催化下, 乙酸酯和β-硅基烯酮发生[4+2]环合反应, 可高立体选择性地合成具有潜在应用价值的β-硅基δ-内酯类化合物. 该方法具有底物简单易得、反应条件温和、底物普适性好和操作简单等优点, 且反应规模放大10倍后也得到了优异的产率和对映体选择性. 该反应产物在氢化还原反应中均呈现出优良的实验结果, 可转化为降血脂药Ezetimibe.

关键词： 氮杂环卡宾; 手性有机硅烷化合物; 不对称催化; β-硅基烯酮; 乙酸酯

本文引用格式

张雨霞 , 郭京程 , 黄杰 , 付振乾 . 氮杂环卡宾催化乙酸酯和β-硅基烯酮的[4+2]环合反应:高立体选择性合成β-硅基δ-内酯[J]. 有机化学, 2021 , 41(11) : 4467 -4475 . DOI: 10.6023/cjoc202105002

Abstract

Asymmetric synthesis of chiral organosilanes with a potential application was realized by N-heterocyclic carbene- catalyzed [4+2] annulation of acetates and β-silyl enones. This strategy exhibits easy to obtain raw materials, mild reaction conditions, good substrate tolerance, simple operation and so on. Notably, excellent yield and enantioselectivity were also observed with expanding the reaction scale by 10 times. The target product showed excellent results in hydrogenation reduction. Moreover, the hypolipidemic drug ezetimibe was obtained through the synthetic transformation of the resulting products.

Key words： N-heterocyclic carbene; chiral organosilanes; asymmetric catalysis; β-silyl enone; acetate

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