研究生: |
王文洋 Wang, Wen-Yang |
---|---|
論文名稱: |
N-保護-3-硝基吲哚和2-氨基苯扎丙酮的不對稱有機催化形式 [4+2] 環加成反應 Asymmetric Organocatalytic Formal [4+2] Cycloaddition of N-protected-3-Nitroindoles and 2-Aminobenzalacetones |
指導教授: |
陳焜銘
Chen, Kwunmin |
口試委員: |
李文山
Li, Wen-Shan 葉怡均 Yeh, Yi-Chun 陳焜銘 Chen, Kwunmin |
口試日期: | 2022/07/26 |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2022 |
畢業學年度: | 110 |
語文別: | 中文 |
論文頁數: | 109 |
中文關鍵詞: | 有機催化 、不對稱合成 、[4+2]環加成 、3-硝基吲哚 、四氫-5H-吲哚并[2,3-b]喹啉 |
英文關鍵詞: | Organocatalysis, Asymmetric synthesis, [4+2] cycloaddition, 3-nitroindole, tetrahydro-5H-indolo[2,3-b]quinoline |
研究方法: | 實驗設計法 |
DOI URL: | http://doi.org/10.6345/NTNU202201094 |
論文種類: | 學術論文 |
相關次數: | 點閱:98 下載:6 |
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近年來,發現一些具有生物活性的天然物,都有著四氫-5H-吲哚并[2,3-b]喹啉的核心骨架。過去的文獻中,對於此類架構合成必須透過金屬催化劑控制立體選擇性,直接使用3-硝基吲哚搭配不對稱有機催化方法尚未被發表。本研究首次展示透過不對稱有機催化形式[4+2]環加成反應,構建四氫-5H-吲哚并[2,3-b]喹啉衍生物。
使用雙功能金雞納生物鹼方醯胺催化劑,對3-硝基吲哚和甲基-2-(甲苯磺酰氨基)苯基α,β-不飽和酮,在溫和的反應條件下,進行鏡像選擇性有機催化反應,合成一系列含有三個連續立體中心的四氫-5H-吲哚并[2,3-b]喹啉衍生物,得到良好的產率(高達60%)和高度立體選擇性(高達15:1 dr和98% ee)。
In recent years, some biologically active natural products have been found to have the core skeleton of tetrahydro-5H-indolo[2,3-b]quinoline. In the past literature, the stereoselectivity must be controlled by metal catalysts for this type of architecture synthesis, and the direct use of 3-nitroindole with asymmetric organocatalysis methods has not been published. This study features the first asymmetric organocatalytic formal for constructed tetrahydro-5H-indolo[2,3-b]quinolines derivatives.
An organocatalytic enantioselective synthesis of tetrahydro-5H-indolo[2,3-b]quinolines derivatives was demonstrated using 3-nitroindoles and methyl 2-(tosylamino)phenyl α,β-unsaturated ketones in the presence of the bifunctional cinchona alkaloids squaramide catalyst. A series of tetrahydro-5H-indolo[2,3-b]quinolines derivatives containing three continuous stereogenic centers were obtained in good yields (up to 60%) and with high stereoselectivities (up to 15:1 dr and up to 98% ee).
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