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| 研究生： |
溫學賢 Wen, Shung-Shien |
|---|---|
| 論文名稱： |
壹. 正四價氧釩錯合物為媒介在Mukaiyama型式醛醇加成反應之應用. 貳.具C2對稱2,6-雙氧-雙環[3,3,0]辛烷掌性模版之研究 (一) vanadium(IV) complex mediated in catalyze asymmetric Mukaiyama aldol addition reaction (二)Study of C2 symmetric 2,6-dioxabicycle[3,3,0]octane as chiral templet |
| 指導教授： |
陳建添
Chen, Chien-Tien |
| 學位類別： |
碩士 Master |
| 系所名稱： |
化學系 Department of Chemistry |
| 畢業學年度： | 87 |
| 語文別： | 中文 |
| 論文頁數： | 161 |
| 中文關鍵詞： | 非鏡像立體選擇性 、醛醇加成反應 、鏡像選擇性 |
| 英文關鍵詞： | Mukayaima aldol addition, VO(acac)2 |
| 論文種類： | 學術論文 |
| 相關次數： | 點閱：1286 下載：0 |
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我們以VO(SO4)·3H2O做為催化劑前驅物與2,2'-雙酚(2,2'-biphenol ) 及三乙基胺之加熱乙氰溶液反應生成之催化劑成功的催化Mukayaima 醛醇加成反應；以苯甲醛及γ-丁酸內酯衍生之矽烷基半縮醛在-20oC下反應12小時可得49%產率，而非鏡像立體選擇性達24/76 ( syn/anti )。而當以N-甲基咪唑代替三乙基胺時以4-硝基苯甲醛和γ-丁酸內酯衍生之矽烷基半縮醛在-20oC反應6小時可定量得到加成產物，和其他芳香醛類反應產率可達70-90%，非鏡像立體選擇性最高可達9/91(syn/anti)。
我們意外發現VO(acac)2在溫和的條件下可亦催化Mukayaima 醛醇加成反應，其催化芳香醛類與γ-丁酸內酯衍生之矽烷基半縮醛可得到適當的產率及非鏡像立體選擇性，其並可做為催化劑的前驅物。在與(R)-O-Acetyl-mandalic acid生成之催化劑於-78oC下催化苯甲醛與γ-丁酸內酯衍生之矽烷基半縮醛加成之反應可得到78%產率及6/94 ( syn/anti )非鏡像立體選擇性，而鏡像選擇性達41%。
Condensation of vanadyl sulfate with 2,2-biphenol in the presence of N-containing ligands provides oxovanadium complexes which serve as efficient catalysts in Mukaiyama aldol reactions to afford aldol products in 78-99% yields with diastereoselectivities of up to 91/9 (anti/syn)
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