研究生: |
林黃櫻 Lin, Huang-Ying |
---|---|
論文名稱: |
利用一價銠金屬經由動力學拆分催化有機硼酸及外消旋環戊烯酮:合成前列腺素及其衍生物 Kinetic Resolution of (±)-4-Siloxy Cyclopentenones Using Rh(I)/Chiral Diene Catalysis: Synthesis of Prostaglandins |
指導教授: |
吳學亮
Wu, Hsyueh-Liang |
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: | 192 |
中文關鍵詞: | 一價銠金屬 、動力學拆分 、外消旋環戊烯酮 、前列腺素 |
英文關鍵詞: | Rh(I), Kinetic Resolution, Prostaglandins |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.072.2018.B05 |
論文種類: | 學術論文 |
相關次數: | 點閱:167 下載:0 |
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本篇論文主要為探討使用一價銠金屬與掌性雙環[2.2.2]配基L2催化芳香性及烯基硼酸試劑68對外消旋起始物(±)-70進行1,4-共軛加成反應(conjugate addition),經由動力學拆分(kinetic resolution),得到化合物109,鏡像選擇性最高達到>99.5%,產率接近50%。將其再利用two-component的方式去合成出目標天然物前列腺素及其衍生物:PGE1 (31; 24% yield), PGA1 methyl ester (65; 9% yield), PGF1α (113; 24% yield)。
This thesis describes the enantioselective conjugate addition reaction of racemic starting material 70 with boronic acid 68 by using Rh(Ⅰ)/L2g catalyst via a with kinetic resolution manner. Compound 109 was obtained with ee up to >99.5% and the yield approximately 50%. This two-component method witnesses its synthetic applications in the synthesis of prostaglandin derivatives: PGE1 (31; 24% yield), PGA1 methyl ester (65; 9% yield), PGF1α (113; 24% yield).
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