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Author: 林黃櫻
Lin, Huang-Ying
Thesis Title: 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
Advisor: 吳學亮
Wu, Hsyueh-Liang
Degree: 碩士
Master
Department: 化學系
Department of Chemistry
Thesis Publication Year: 2018
Academic Year: 106
Language: 中文
Number of pages: 192
Keywords (in Chinese): 一價銠金屬動力學拆分外消旋環戊烯酮前列腺素
Keywords (in English): Rh(I), Kinetic Resolution, Prostaglandins
DOI URL: http://doi.org/10.6345/THE.NTNU.DC.072.2018.B05
Thesis Type: Academic thesis/ dissertation
Reference times: Clicks: 198Downloads: 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).

目錄 中文摘要 1 Abstract 2 表目錄 5 圖目錄 7 中英文縮寫對照表 11 第一章 緒論 15 第二章 文獻回顧 27 第三章 實驗設計與概念 44 第四章 實驗結果與討論 65 第五章 合成應用 103 第六章 立體化學之探討 114 第七章 結論 119 第八章 實驗部分 121 第九章 參考文獻 189

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