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| 研究生： |
張富傑 Chang, Fu-Jie |
|---|---|
| 論文名稱： |
有機催化連鎖1,6/1,4/1,2/1,2-加成反應生成多取代之三環化合物 Diastereoselective Synthesis of Functionalized Angularly Fused Tricycles via an Organocascade Quadruple Reaction Involving Vinylogous 1,6/1,4/1,2/1,2-Addition Sequence |
| 指導教授： |
陳焜銘
Chen, Kwun-Min |
| 學位類別： |
碩士 Master |
| 系所名稱： |
化學系 Department of Chemistry |
| 論文出版年： | 2016 |
| 畢業學年度： | 104 |
| 語文別： | 中文 |
| 論文頁數： | 116 |
| 中文關鍵詞： | 有機連鎖反應 、1,6-加成反應 、三環 |
| 英文關鍵詞： | Organocascade, 1,6-addition, tricyclic |
| DOI URL： | https://doi.org/10.6345/NTNU202203973 |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：99 下載：0 |
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藉由三個分子化合物，進行有機連鎖四階反應，發展高非鏡像選擇性官能基的直並連三環化合物。使用1,3-茚二酮雙烯化合物與乙醯乙酸乙酯，利用20 mol%的硫尿素衍生之有機催化劑及加入20 mol%的1,4-二氮雜二環[2.2.2]辛烷，進行1,6/1,4/1,2/1,2-連鎖反應，得到密集官能基的三環化合物，有優異的產率（高達94%）及非鏡像選擇性（高達>20:1 dr）。此外，也經由單晶繞射X-ray確認其產物相對立體組態；然而，關於鏡像選擇性之有機連鎖反應仍在進行當中。
An efficient three components organocascade quadruple reaction has been developed and successfully accessed to the highly diastereoselective functionalized tricyclic compounds. The reaction between arylallylidene-indane-1,3diones and ethyl acetoacetate mediated by thiourea derived organocatalyst and DABCO via 1,6-/1,4-/1,2-/1,2-addition sequence to generate densely functionalized tricyclic outcomes with good yields (up to 94%) and excellent diastereoselectivities (up to >20:1 dr). The relatived configuration of the cyclized product was determined by the single crystal X-ray analysis. However, the enantiomeric version of the organocascade reaction is currently under investigation in our laboratory.
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