研究生: |
張景智 Chang, Ching-Chih |
---|---|
論文名稱: |
經由一價銠金屬催化聯繼芳基環化與β-乙醯氧基消去反應合成具全碳四級立體中心之掌性茚化合物 Enantioselective Synthesis of All-Carbon Quaternary Indenes via Rhodium(I)-Catalyzed Tandem Arylative Cyclization and β-Acetoxy Elimination |
指導教授: |
吳學亮
Wu, Hsyueh-Liang |
口試委員: |
林民生
Hayashi, Tamio 謝仁傑 Hsieh, Jen-Chieh 吳學亮 Wu, Hsyueh-Liang |
口試日期: | 2022/09/05 |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2022 |
畢業學年度: | 110 |
語文別: | 中文 |
論文頁數: | 255 |
中文關鍵詞: | 一價銠金屬催化 、不對稱芳基環化反應 、全碳四級立體中心 、掌性茚化合物 、β-乙醯氧基消去反應 、含有醯胺基的掌性雙環[2.2.1]雙烯配基 |
英文關鍵詞: | Rhodium(I)-catalyzed, asymmetric arylative cyclization, an all-carbon quaternary stereocenter, chiral indenes, β-acetoxy elimination, bicyclo[2.2.1]heptadiene ligand |
研究方法: | 實驗設計法 、 準實驗設計法 |
DOI URL: | http://doi.org/10.6345/NTNU202201723 |
論文種類: | 學術論文 |
相關次數: | 點閱:118 下載:6 |
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本篇論文使用一價銠金屬及含醯胺取代的掌性雙環[2.2.1]雙烯配位基L2a形成之催化劑,並加入三乙胺作為添加劑,以甲醇作為溶劑,於反應溫度40 ℃之條件下,催化炔類化合物2與芳基硼酯化合物1進行不對稱聯繼芳基環化與β-乙醯氧基消去反應,最終生成一系列具全碳四級立體中心的掌性茚化合物3。總共有27個例子,產物產率介於17–99%,鏡像超越值最高達98%,產物位置選擇性最佳比例則為20:1。
This thesis describes an enantioselective tandem arylative cyclization of arylboronates derivatives 1 with internal alkynes 2 in MeOH at 40 °C employing triethylamine as an additive in presence of 3.0 mol% of Rh(I)-catalyst in situ generated from the [Rh(C2H4)2Cl]2 and the chiral bicyclo[2.2.1]heptadiene ligand bearing a benzylamide group L2a. This synthetic protocol offers a facile way to provide a series of chiral indene derivatives 3 with an all-carbon quaternary stereocenter in 17–99% yields, up to 98% ee and with up to regioselective ratio of 20:1.
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