研究生: |
林育賢 Lin, Yu-Sian |
---|---|
論文名稱: |
高度非鏡像選擇性有機催化[2+2+2]環化反應合成全取代螺環吲哚酮 Highly Diastereoselective Synthesis of Fully Substituted Spirocyclic Oxindole via Organocatalysis [2+2+2] Annulation Reaction |
指導教授: |
陳焜銘
Chen, Kwunmin |
口試委員: |
陳焜銘
Chen, Kwunmin 杜玲嫻 Tu, Ling-Hsien 李文山 Li, Wen-Shan |
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: | 94 |
中文關鍵詞: | 有機催化連鎖反應 、螺環吲哚酮 |
英文關鍵詞: | cascade, spirocyclic oxindoles |
研究方法: | 實驗設計法 |
DOI URL: | http://doi.org/10.6345/NTNU202200966 |
論文種類: | 學術論文 |
相關次數: | 點閱:179 下載:17 |
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此論文成功開發全取代螺環吲哚酮衍生物的合成方法,並且得到兩個四級碳中心,透過有機催化連鎖反應,進行 Michael/Michael/1,2-addition 反應。在 0 ℃的條件下,使用丙二腈、苄烯丙二腈、(E)-3-苄基-1-叔丁氧羰基-2-吲哚酮作為起始物,並以乙腈作為溶劑,加入催化量(30 mol%)的四甲基乙二胺,反應 8到 20 小時,製備全取代螺環吲哚酮衍生物,得到中等到良好的產率(45 - 81 %)、良好的非鏡像選擇性(14:1 - >20:1 d.r.)。
An efficient cascade protocol between malononitrile, benzylidenemalononitrile, and (E)-tert-butyl-3-benzylidene-2-oxoindoline-1-carboxylate has been developed. Fully substituted spirocyclic oxindole derivative bear two all-carbon quaternary centers. The reaction proceeds through a Michael/Michael/1,2-addition reaction. The spirocyclic oxindole derivatives were obtained in reasonable-to-good chemical yields (45 - 81 %) and high levels of diastereoselectivities (14:1 - >20:1 d.r.) using a catalytic amount of commercially available TMEDA (30 mol%) in ACN at 0 ℃ for 8 - 20 h.
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