一、 以掌性硫化合物進行不對稱 [4+1] 環化反應並應用在吲哚啉類化合物的合成研究二、掌性共價有機框架材料的設計與合成並應用在多烯環化反應

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謝欣翰(Hsin-Han Hsieh) 查詢紙本館藏

畢業系所

化學學系

論文名稱

一、以掌性硫化合物進行不對稱 [4+1] 環化反應並應用在吲哚啉類化合物的合成研究二、掌性共價有機框架材料的設計與合成並應用在多烯環化反應
((Thiolan-2-yl)diphenylmethanol Benzyl Ether-Catalyzed Asymmetric [4+1] Cyclization and Its Application for Synthesis of Indoline derivativeDesign and Synthesis of Chiral Covalent Organic Frameworks and Its Application for Asymmetric Polyene Cyclization)

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摘要(中)

在不對稱環化反應中硫偶極體常被當作碳原子的合成子，藉由硫偶極
體的親核基加成到具有親電性的起始物上進行環氧化合物、氮丙啶化合物
以及環丙烷化合物的合成。論文中使用實驗室所發表以及開發的掌性硫化
物，將此掌性硫化物應用在過渡金屬的不對稱 [4+1] 環化反應中，希望能
開發出更多的應用性。
在大自然中許多具有生物活性的萜類化合物都是經由酵素對異戊二烯
類的化合物進行環化反應。而此多烯環化的反應一直被認為是合成具有生
物活性的萜類化合物和其他天然物的重要反應，藉由多烯環化的反應能夠
有效的將分子中的碳進行鍵結同時控制其立體結構。受到 William R.
Dichtel’s 的研究所啟發，我們使用 1,1′-聯-2-萘酚為基底的單體與三烯化合
物作為架橋分子，利用環合置換反應將兩種化合物進行鍵結合成出掌性共
價有機框架材料，將其應用在多烯環化反應中並且探討異相催化劑在多烯
環化的應用及發展性。

摘要(英)

Sulfur ylides have long been used as one-carbon synthons in many kinds of
transformations, such as synthesis of epoxides, aziridines, and cyclopropanes
through ylide addition to the electron-poor π system. Our lab has previously
reported the enantioselective synthesis of (S)-thionyl diphenylmethanol and the
application of its benzyl ether derivative in asymmetric synthesis, catalytic CoreyChaykovsky reaction of benzyl bromide, and aldehydes to give trans-epoxides in
high yield with good to high enantiomeric excess. The ability of sulfur-based
ylides to efficiently participate in transition metal-catalyzed [4+1] cycloaddition
was found recently. Further extension of the application of this chiral sulfide to
participate in transition metal-catalyzed [n+1] cycloaddition is explored by using
our catalyst (THTOBn) or its sulfonium salt in this thesis.
A variety of terpenoids are enzymatically synthesized by cyclization of
polyprenoids such as squalene, farnesol, geranylgeraniol in the biological system.
Polyene cyclization is recognized as a unique and efficient way to build structural
complexity from acyclic molecules via concerted and stereo-controlled C–C bond
formations. In this work, we use a new type of porous material, chiral covalent
organic frameworks (CCOFs) as a chiral source and catalyst to conduct polyene
cyclization. Inspired by William R. Dichtel’s work, we plan to adopt ring-closing
metathesis strategy for the construction of CCOFs from 1,1′-Bi-2-naphthol
(BINOL) type monomers and triene linkers.

關鍵字(中)

★ 硫偶極體
★ 掌性
★ 環化反應
★ 多烯環化
★ 共價有機框架材料

關鍵字(英)

★ Sulfur ylide
★ Chiral
★ Cycloaddition
★ Polyene cyclization
★ Covalent organic frameworks

論文目次

中文摘要.....................................................................................................................................i
Abstract.......................................................................................................................................ii
謝誌...........................................................................................................................................iii
總目錄.......................................................................................................................................iv
圖目錄......................................................................................................................................vii
式目錄.......................................................................................................................................ix
表目錄........................................................................................................................................x
縮寫說明..................................................................................................................................xii
第一章掌性硫化合物進行不對稱 [4+1] 環化反應......................................................1
第一節緒論.......................................................................................................................1
1-1 硫偶極體的發現與應用................................................................................................1
1-2 硫偶極體的 [2+1] 不對稱環化反應...........................................................................4
1-2-1 硫偶極體的不對稱環氧化反應...........................................................................4
1-2-2 硫偶極體的不對稱氮丙啶化反應.......................................................................7
1-2-3 硫偶極體不對稱環丙烷化反應.........................................................................10
1-3 硫偶極體的不對稱 [n+1] 環化反應.........................................................................12
1-4 研究動機......................................................................................................................21
第二節結果與討論................................................................................................................23
2-1 手性硫化物的製備與合成路徑..................................................................................23
2-2 乙烯基氨基甲酸酯 (vinyl carbamates) 的合成........................................................25
v
2-3 不對稱 [4+1] 環化反應.............................................................................................26
2-3-1 不對稱 [4+1] 環化反應的溫度篩選................................................................26
2-3-2 不對稱 [4+1] 環化反應的金屬催化劑量的篩選............................................28
2-3-3 不對稱 [4+1] 環化反應的溶劑篩選................................................................29
2-3-4 不對稱 [4+1] 環化反應的鹼篩選....................................................................31
2-3-5 不對稱 [4+1] 環化反應的優化........................................................................33
2-3-6 不對稱 [4+1] 環化反應機構探討....................................................................35
2-4 不對稱 [4+1] 環化反應的催化量嘗試.....................................................................37
2-4-1 不對稱 [4+1] 環化反應的催化量策略............................................................37
2-4-2 不對稱 [4+1] 環化反應的催化量嘗試............................................................38
2-4-3 不對稱 [4+1] 環化反應的催化量催化循環式意圖........................................44
第三節結論............................................................................................................................45
第二章掌性共價有機框架材料的設計與合成並應用在多烯環化反應............................46
第一節緒論.......................................................................................................................46
1-1 掌性共價有機框架材料 (CCOFs) 的發展背景.......................................................46
1-2 掌性共價有機框架材料 (CCOFs) 的建構方法.......................................................47
1-3 掌性共價有機框架材料 (CCOFs) 的合成介紹.......................................................51
1-4 掌性共價有機框架材料 (CCOFs) 的催化反應應用...............................................54
1-5 研究動機......................................................................................................................59
第二節結果與討論................................................................................................................62
2-1 單體與架橋分子設計與合成......................................................................................62
2-2 掌性共價有機框架材料的合成與應用......................................................................69
vi
2-3 掌性共價有機框架材料合成條件與多烯環化條件的篩選......................................76
2-4 掌性共價有機框架材料的多烯環化反應示意圖......................................................78
第三節結論............................................................................................................................80
第三章實驗部分....................................................................................................................81
3-1 General information ......................................................................................................81
3-2 Procedure and spectroscopic data .................................................................................82
第四章參考文獻..................................................................................................................109
附錄........................................................................................................................................121

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指導教授

陳榮傑謝發坤(Rong-Jie Chein Fa-Kuen Shieh)

審核日期

2021-9-29

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