經2-萘酚和2-羥基苯甲醛衍生物合成鏻鹽作為威悌反應試劑前驅物及其應用於威悌反應合成9H-二苯并哌喃衍生物 發展亞胺葉立德前驅物及1,3茚二酮衍生物的有機鹼催化劑控制之多樣性導向(3+2)環化反應: Chromenopyrrolidines的合成
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2020
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第一章: 9H-二苯并哌喃之相關化合物具有作為螢光染劑及醫療的功能，過去多以金屬催化的方式進行合成，而在過往的文獻中，我們也發現要在此結構上建構碳碳雙鍵需要較為繁複的合成步驟，我們在實驗中藉由合成磷鹽起始物進行威悌反應來得到相關產物，而此方法也是過去建構雙鍵於9H-二苯并哌喃結構上時較少被使用過的策略，我們成功以非金屬的反應方式，利用較少步驟合成出具有E/Z兩種異構物的產物。
關鍵字: 9H-二苯并哌喃、威悌反應、磷鹽。
第二章: 亞胺葉立德在過去多用於進行(3+2)的合環反應，而其反應位向經常受到電子效應之影響，而傾向於特定的反應位向，我們利用多樣性合成的概念，利用改變鹼性催化劑的方式，分別以4-二甲氨基吡啶(DMAP)和四甲基胍(TMG)成功調控反應位向，得到兩種具有高度位向選擇性之Chromenopyrrolidines衍生物，能在溫和的反應下進行且不使用金屬試劑。
9H-xanthenes can be used as fluorescent dyes or act as medicines. 9H-xanthene derivatives were often prepared using metal catalysis as the key step in multiple step synthesis. Herein we report a novel, metal-free synthesis of 9H-xanthene derivatives alkylidenes using Wittig reactions from the corresponding phosphonium salts. A series of highly functional (E/Z)-9H-xanthene alkylidene derivatives were successfully synthesized in mild reaction condition. Keyword: 9H-xanthenes, Wittig reaction, phosphonium salts. Azomethine ylide mostly used in (3+2) cycloaddition in the past. The electronic effect often influenced the reaction position and resulted in specific product. We used the concept of diversity-oriented synthesis to change the base catalyst and successfully got two regiodivergent Chromenopyrrolidines product with high selectivity. The reaction can proceed in mild condition without using any metal reagent.
9H-xanthenes can be used as fluorescent dyes or act as medicines. 9H-xanthene derivatives were often prepared using metal catalysis as the key step in multiple step synthesis. Herein we report a novel, metal-free synthesis of 9H-xanthene derivatives alkylidenes using Wittig reactions from the corresponding phosphonium salts. A series of highly functional (E/Z)-9H-xanthene alkylidene derivatives were successfully synthesized in mild reaction condition. Keyword: 9H-xanthenes, Wittig reaction, phosphonium salts. Azomethine ylide mostly used in (3+2) cycloaddition in the past. The electronic effect often influenced the reaction position and resulted in specific product. We used the concept of diversity-oriented synthesis to change the base catalyst and successfully got two regiodivergent Chromenopyrrolidines product with high selectivity. The reaction can proceed in mild condition without using any metal reagent.
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9H-二苯并哌喃, 威悌反應, 磷鹽, 亞胺葉立德, 多樣性合成, 9H-xanthenes, Wittig reaction, phosphonium salts, azomethine ylide, diversity-oriented synthesis