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研究生： 柳彥成
Liou, Yan-Cheng
論文名稱： (一) 使用鄰羥基對亞甲基苯醌經由 1,6-膦加成/氧-醯化/威悌反應建構官能化苯并呋喃衍生物 (二) 膦催化之化學選擇性還原/亞硝酸離去/威悌反應建構 3-烯基苯并呋喃衍生物 (三) 亞烷基米氏酸與亞胺葉立德經 (3+2) 環加成/內酯化反應合成高鏡像選擇性之𠳭酮[4,3-b]吡咯啶
I. Synthesis of Functionalized Benzofurans from para-Quinone Methides via Phospha-1,6-Addition/O-Acylation/Wittig Pathway II. Phosphine-catalyzed Chemoselective Reduction/Elimination/Wittig Reaction Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans III. Enantioselective Construction of Chromeno[4,3-b]pyrrolidines from Meldrum’s Acid Alkylidenes and Azomethide Ylides via the (3+2) Cycloaddition/Lactonization Pathway
指導教授： 林文偉
Lin, Wenwei
口試委員： 林文偉
Lin, Wenwei
張永俊
Jang, Yeong-Jiunn
陳焜銘
Chen, Kwunmin
姚清發
Yao, Ching-Fa
劉維民
Liu, Wei-Min
口試日期： 2022/07/15
學位類別： 博士
Doctor
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： 310
中文關鍵詞： 苯并呋喃 、膦試劑 、分子內威悌反應 、對亞甲基苯醌 、3-烯基苯并呋喃 、催化膦 、威悌反應 、亞硝酸脫除 、亞胺葉立德 、米氏酸 、不對稱催化 、𠳭酮[4,3-b]吡咯啶
英文關鍵詞： 1,6-Addition, 2,3-Diarylbenzofuran, Wittig reaction, Catalytic Wittig reaction, Nitrous acid elimination, 3-Alkenylbezofuran, Chromeno[4,3-b]pyrrolidine, Asymmetric catalyst, Azomethide ylide, Meldrum’s acid
研究方法: 實驗設計法 、 行動研究法
DOI URL： http://doi.org/10.6345/NTNU202201092
論文種類： 學術論文
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    • (一)穩定的鄰羥基對亞甲基苯醌化合物通過有機膦、醯氯和鹼處理，在無金屬且溫和條件下，有效合成官能化的苯并呋喃。同時，在催化條件下亦證明此一鍋化法之1,6-膦加成/氧-醯化/威悌反應，具有相似的合成官能化苯并呋喃的功效。

    (二)經由使用催化量的膦試劑進行分子內威悌反應，提供在無金屬條件下建構官能化 3-烯基苯并呋喃的有效方法。該一鍋化反應是通過將有機膦進行麥可加成到氧-醯化之硝基苯乙烯而引發，其中膦是通過用苯基矽烷對氧化膦進行化學選擇性還原而生成，從而產生膦葉立德，通過氧-醯化/亞硝酸消除/威悌反應製備多官能化的 3-烯基苯并呋喃衍生物。

    (三)亞烷基米氏酸與亞胺葉立德經由硫脲片段衍生之金雞納鹼催化下，在短時間內進行 (3+2) 環加成/酯交換反應，在短時間內建構優異產率與鏡像選擇性之𠳭酮[4,3-b]吡咯啶衍生物。此外，我們根據實驗結果的發現，提出了催化劑與亞烷基米氏酸活化的反應模型。

    (一)An efficient synthesis of functionalized benzofurans is achieved under mild and metal free conditions from stable para-quinone methides by treatment with phosphine, acyl chloride, and a base. This one-pot phospha-1,6-addition/O-acylation/Wittig reaction is also demonstrated under catalytic conditions with similar efficacy.

    (二)A highly efficient protocol for the synthesis of functionalized 3-alkenyl benzofurans is demonstrated under metal-free conditions using catalytic amount of phosphine proceeding an intramolecular Wittig reaction. This one-pot reaction was initiated by the phospha-Michael addition of phosphine to O-acylated nitrostyrene, in which phosphine was in-situ generated from the chemoselective reduction of phosphine oxide with PhSiH3, would provide the phosphorus ylide to result in the aforementioned multifunctionalized benzofuran via O-acylation/nitrous acid elimination/Wittig reaction.

    (三)A quinine-derived thiourea-catalyzed enantioselective (3+2) cycloaddition/desymmetrization transesterification reaction of Meldrum’s acid alkylidenes with azomethine ylides is realized in minute-scale. The desired chromeno[4,3-b]pyrrolidines were obtained in moderate to excellent yields with excellent stereoselectivities. Moreover, a plausible dual activation catalytic model via the hydrogen bonding interaction of the moiety of catalyst towards Meldrum’s acid alkylidene was proposed according to the findings in this study.

    序章 1 膦試劑用於建構碳-碳單鍵 1 膦試劑用於建構碳-碳雙鍵 2 膦試劑用於進行官能基轉換 3 膦試劑用於合成雜環 5 第一部分 使用鄰羥基對亞甲基苯醌經由 1,6-膦加成/氧-醯化/威悌反應建構官能化苯并呋喃衍生物 9 1-1 前言 9 1-1-1 對亞甲基苯醌之介紹 9 1-1-2 鄰羥基之 p-QMs 用於合成雜環 10 1-1-3 2,3-二芳基苯并呋喃之生物活性 12 1-1-4 2,3-二芳基苯并呋喃之合成方式 12 1-2 研究動機 13 1-3 研究結果與討論 15 1-3-1反應條件優化－膦試劑與溶劑篩選 15 1-3-2反應條件優化－鹼試劑與其當量數及其他條件的篩選 16 1-3-3醯氯取代基效應探討 18 1-3-4 使用催化量的膦試劑進行反應 20 1-3-5反應機構探討 21 1-4結論 26 1-5 光譜解析 26 1-6 實驗部分 31 1-6-1 分析儀器 31 1-6-2 實驗操作步驟 31 1-6-3 光譜數據 32 參考文獻 49 附件一、NMR光譜數據 52 附件二、X-ray 單晶繞射數據 72 附件三 檢查清單 74 第二部分 膦催化之化學選擇性還原/亞硝酸離去/威悌反應建構 3-烯基苯并呋喃衍生物 75 2-1 前言 75 2-1-1 硝基官能團在合成上的應用 75 2-1-2 硝基烷做為拉電子基團及親核性前驅物的應用 76 2-1-3 硝基烯烴的應用 77 2-1-4 硝基化合物在雙鍵建構的應用 78 2-2 研究動機 80 2-3 研究結果與討論 84 2-3-1 反應條件優化－膦試劑當量及反應溫度篩選 84 2-3-2 反應條件優化－溶劑篩選 85 2-3-3 催化膦系統介紹 88 2-3-4 催化膦系統應用於分子內 Wittig 反應之條件優化 90 2-3-5 鄰-羥基硝基苯乙烯於催化型 Wittig 反應之取代基效應探討 93 2-3-6 克級合成 97 2-3-7 反應機構探討 97 2-4結論 101 2-5 光譜解析 102 2-6 實驗部分 106 2-6-1 分析儀器 106 2-6-2 實驗操作步驟 106 2-6-3 光譜數據 110 參考文獻 143 附件一、NMR 光譜數據 145 附件二、 X-ray 單晶繞射數據 187 附件三 檢查清單 189 第三部分 亞烷基米氏酸與亞胺葉立德經 (3+2) 環加成/內酯化反應合成高鏡像選擇性之𠳭酮[4,3-b]吡咯啶 190 3-1 前言 190 3-1-1 有機催化概述 190 3-1-2 Chromenopyrrolidines的介紹 191 3-1-3 1,3-偶極體介紹 192 3-1-4米氏酸介紹 199 3-1-4-1 米氏酸作為試劑 200 3-1-4-2 亞烷基米氏酸在合成上的應用 201 3-2 研究動機 202 3-3 結果與討論 203 3-3-1 反應條件優化-催化劑篩選 203 3-3-2 反應條件優化-溶劑篩選 205 3-3-3 反應條件優化-濃度與催化劑使用量 206 3-3-4 反應條件優化-起始物當量篩選 207 3-3-5 取代基效應探討 209 3-3-6 克級合成 211 3-3-7 118a 之鏡像異構物之合成 212 3-3-8 反應機構探討 212 3-4 未來展望 213 3-5 結論 214 3-6 光譜解析 215 3-7 實驗部分 221 3-7-1 分析儀器 221 3-7-2 實驗操作步驟 222 3-7-3 光譜數據 226 參考文獻 253 附件一、NMR 光譜資料 255 附件二、X-ray 單晶繞射數據 281 附件三、高效液相層析 (HPLC) 數據 282 附件四、檢查清單 309 附件五、博士班期間完成的論文發表 310

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