研究生: |
余純瑋 Yu, Chun-Wei |
---|---|
論文名稱: |
鏡像選擇合成呋喃[2,3-b]呋喃結構經由Michael/縮醛化/縮醛化連鎖反應 Enantioselective Synthesis of Furo[2,3-b]furan Scaffolds via Michael/Acetalization/Acetalization Cascade Reaction |
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: | 2018 |
畢業學年度: | 106 |
語文別: | 中文 |
論文頁數: | 131 |
中文關鍵詞: | Michael反應 、有機連鎖反應 、縮醛化 、六環 、呋喃[2,3-b]呋喃 |
英文關鍵詞: | Michael reaction, Organocascade, Acetalization, hexacyclic, Furo[2,3-b]furan |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.028.2018.B05 |
論文種類: | 學術論文 |
相關次數: | 點閱:92 下載:0 |
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本實驗室成功利用Michael/縮醛化/縮醛化連鎖反應,使用低毒性溶劑及溫和反應條件,建構出連續六環呋喃[2,3-b]呋喃結構衍生物,有四個立體中心,具有適中的產率及良好至優異的鏡像超越值。反應以1,3-茚二酮衍生物(1.5 equiv.)及β-四氫萘酮(1.0 equiv.)於甲苯溶劑下,使用奎寧衍生之方烯胺有機掌性氫鍵催化劑(20 mol%),反應4小時後,可得到連續六環呋喃[2,3-b]呋喃結構衍生物,產率最高可達86%,鏡像超越值最高可達97%ee,經由再結晶純化可達> 99.5% ee。更多相關研究於本實驗室進行中。
Our lab successfully synthesized continuous hexacyclic furo[2,3-b]furan scaffold derivatives with four stereogenic centers via Michael/acetalization/acetalization cascade reations. Reaction starting materials were 1,3-indanedion derivatives (1.5 equiv.) and β-tetralone(1.0 equiv.) which were stirred in toluene and used quinine derived squaramide as hydrogen bond organocatalyst. After reaction lasting for 4 hours, continuous hexacyclic furo[2,3-b]furan scaffold derivatives formed with up to 86% yield and up to 97% ee . The enantiomeric excess could be enhanced to over 99.5% ee by recrystalization. The absolute configurations of the cyclized product was determined by the single crystal X-ray analysis. Further related researches are underway in our lab.
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