云南大学学报(自然科学版)2024,Vol.46Issue(2) :319-326.DOI:10.7540/j.ynu.20230062

有机催化串联反应构建螺[环丙烷-氧化吲哚]类化合物的研究

Synthesis of spiro[cyclopropane-oxyindole]compounds by organic catalytic reaction

陈治明
云南大学学报(自然科学版)2024,Vol.46Issue(2) :319-326.DOI:10.7540/j.ynu.20230062

有机催化串联反应构建螺[环丙烷-氧化吲哚]类化合物的研究

Synthesis of spiro[cyclopropane-oxyindole]compounds by organic catalytic reaction

陈治明1
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作者信息

  • 1. 贵州师范大学化学与材料科学学院,贵州省功能材料化学重点实验室,贵州贵阳 550001
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摘要

成功设计合成了 4种C2 轴手性结构上下对称的硫脲催化剂,并将其用于不对称催化构建螺[环丙烷-氧化吲哚]类化合物的合成.实验结果表明,在室温25℃下,x=10%3a作为催化剂,溶剂为CHCl3,合成的螺[环丙烷-氧化吲哚]得到较好的产率(89%)和较高的对映选择性(87%).该反应具有环境友好、反应条件温和、催化剂廉价易得等优点.该方法为具有生物药理活性的螺[环丙烷-氧化吲哚]骨架的合成提供了重要途径.

Abstract

In this paper,four thiourea catalysts containing chiral carbon and C2 chiral axis were designed and synthesized successfully,and they were used for the asymmetric synthesis of spiral[cyclopropane-indole oxide]compounds.The experimental results showed that the synthesis of spiro[cyclopropane-oxyindole]obtained better yield(89%)and higher enantioselectivity(87%)at room temperature 25℃with 10 mol%3a as catalyst and CHCl3 as solvent.The reaction has the advantages of friendly environment,mild reaction condition and cheap catalyst.This method provides an important way for the synthesis of snail[cyclopropane-oxyindole]skeleton with biological pharmacological activity.

关键词

螺[环丙烷-氧化吲哚]类化合物/不对称催化/硫脲催化剂

Key words

cyclopropane-oxyindole compounds/asymmetric catalysis/thiourea catalysts

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基金项目

国家自然科学基金(21362006)

出版年

2024
云南大学学报(自然科学版)
云南大学

云南大学学报(自然科学版)

CSTPCDCSCD北大核心
影响因子:0.663
ISSN:0258-7971
参考文献量18
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