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| 研究生： |
王子平 Wang, Tzu-Ping |
|---|---|
| 論文名稱： |
利用金雞納鹼衍生的雙官能基催化劑進行有機不對稱催化反應建構苯并哌喃 [3,4-d] 吡咯衍生物 Enantioselective Synthesis of Chromeno[3,4-d]pyrrole Derivatives by Using Cinchona Alkaloid Derived Bifunctional Organocatalyst |
| 指導教授： |
林文偉
Lin, Wen-Wei |
| 學位類別： |
碩士 Master |
| 系所名稱： |
化學系 Department of Chemistry |
| 論文出版年： | 2016 |
| 畢業學年度： | 104 |
| 語文別： | 中文 |
| 論文頁數： | 267 |
| 中文關鍵詞： | 有機不對稱 、金雞納鹼 、苯并哌喃 、雙官能基催化劑 |
| 英文關鍵詞： | Bifunctional Organocatalyst |
| DOI URL： | https://doi.org/10.6345/NTNU202204350 |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：165 下載：0 |
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在第一章節中，我們使用一新穎的串聯反應來合成苯并哌喃 [3,4-d] 吡咯衍生物，此反應擁有很高的產率、鏡像及非鏡像選擇性。在溫和的反應條件下，此串連反應可以有效的建立 6 個立體中心，其中包含 5 個四級碳中心的產物。
在第二章節中，一新穎的催化 Michael 加成-異構化反應，有效地合成 Rauhut-Currier 類型的產物，此反應得到少見的γ-不飽和丁內醯胺進行 alfa位置加成產物，並擁有很好的非鏡像選擇性。此反應還能進一步經由水解後脫脫羧，得到不能由一般查耳酮合成出的alfa加成產物。
In the first chapter, a novel cascade reaction was developed for the synthesis of chromeno[3,4-d]pyrrole in high yields and with excellent enantioselectivities. Under mild conditions, the cascade reactions efficiently established six stereogenic centers including five quaternary stereocenter in the expected products.
In the second chapter, a novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. It was quite unexpected to see the α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.
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