| 研究生: |
宋品樺 sung, pin-hua |
|---|---|
| 論文名稱: |
合成L-Proline的衍生物並應用於Aldol及Michael reactions的不對稱催化反應 Synthesis of L-Proline derivatives and their applications on Asymmetric Aldol and Michael reactions |
| 指導教授: |
宋光生
Sung, Kuangsen |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 化學系 Department of Chemistry |
| 論文出版年: | 2009 |
| 畢業學年度: | 97 |
| 語文別: | 中文 |
| 論文頁數: | 74 |
| 中文關鍵詞: | 直接進行aldol反應 、二胜肽 、鏡像物選擇反應 |
| 外文關鍵詞: | Direct, Dipeptide, Enantioselective reaction, aldol reaction |
| 相關次數: | 點閱:62 下載:2 |
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合成數個由L-Proline所衍生的二胜肽,並探討其在Aldol reactions不對稱催化的產率及鏡像異構物的選擇性;發現在低溫下長時間反應可以得到較佳的產率及ee值,其中以L-Pro-L-Phe表現最好,且因為取代基的立體效應造成L-Proline-L-amino acid在ee值上比L-Proline-D-amino acid為佳,DMSO為溶劑比其他具有氫鍵的溶劑為理想。而二胜肽也被應用在Michael reaction的不對稱催化,比較產率及ee值後,以L-Pro-L-Val為較佳的催化劑;另外也將L-Proline接在聚合物上來催化Michael reaction,在產率上有九成以上,但ee值偏低。
This thesis involves synthesis of some of L-Proline-derived dipeptides, and discussion about their yield and enantioselective direct aldol reactions. We found that reactions have better yield and enantioselectivity in the condition of low temperature and long reaction time. The best catalyst of those was L-Pro-L-Phe. L-Proline-L-amino acids as catalysts could have better enantioselectivity than L-ProlineD-amino acids, because the steric effect of substituent groups on the amino acids.
DMSO was the ideal solvent than other solvents that have hydrogen bonding.
Dipeptides were also applied to asymmetric synthesis of Michael reaction. Compare the yields and enantiomeric excess, L-Pro-L-Val was the better catalyst. In addition, L-Proline which is connected to a polymer catalyzes Michael reaction, and the yield was up to 90 %, but the enantiomeric excess was low.
1. 楊登貴等多位學者,不對稱合成與催化,中興大學文教基金會
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