Author: |
黃千益 Huang, Chien-Yi |
---|---|
Thesis Title: |
經由[3+3]硫尿素有機催化下合成非鏡像選擇性之螺環茚吡喃併吡唑化合物 Diastereoselective Synthesis of Dihydrospiro[indene-2,4’-pyrano[2,3-c]pyrazole]-1,3-dione Scaffolds via [3+3] Thiourea-Catalyzed Annulation |
Advisor: |
陳焜銘
Chen, Kwun-Min |
Degree: |
碩士 Master |
Department: |
化學系 Department of Chemistry |
Thesis Publication Year: | 2018 |
Academic Year: | 106 |
Language: | 中文 |
Number of pages: | 123 |
Keywords (in Chinese): | 有機連鎖反應 、[3+3]加成反應 、螺環化合物 |
Keywords (in English): | Spirocompound, [3+3]-Annulation, Diasteroselcetivity |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.029.2018.B05 |
Thesis Type: | Academic thesis/ dissertation |
Reference times: | Clicks: 128 Downloads: 0 |
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本實驗室藉由兩個有機小分子進行有機連鎖反應,發展出高非鏡像選擇之螺環茚吡喃併吡唑化合物。使用吡唑酮與四取代烯烴,利用 20 mol %的硫尿素衍生之有機催化劑及20 mol %的 4-二甲氨基吡啶,經由[3+3]合環反應,Michael/Acetalization 反應,生成多官能基的螺環茚吡喃併吡唑化合物,其具有不錯的產率(高達 94 %)及優異的非鏡像選擇性(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。而螺環茚吡喃并吡唑化合物尚未有相關文獻報導,期許此方法能應用於天然物之合成上。
An organocascade reaction between pyrazolone and arylallylilidene-indene-1,3-diones derivated tertiary substituted alkene has been developed to a [3+3]-cycloaddtion leading functionalized dihydrospiro[indene-2,4'-pyrano[2,3-c]pyrazole]-1,3-dione frameworks. The reaction mediated by thiourea derived organocatalyst proceeds via Michael/Acetalization reaction in high yields and with excellent diasteroslectivity (up to >20:1dr). The relatived configuration of the cyclized product was determined by the single crystal X-ray analysis
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