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研究生: 張瓊安
Chang, Chiung-An
論文名稱: 掌性銠金屬雙烯錯合物催化不對稱加成反應
Asymmetric Transformations Catalyzed by Rh(I)/Chiral Dienes
指導教授: 吳學亮
Wu, Hsyueh-Liang
學位類別: 博士
Doctor
系所名稱: 化學系
Department of Chemistry
論文出版年: 2018
畢業學年度: 106
語文別: 中文
論文頁數: 199
中文關鍵詞: 共軛加成酮酯化合物硼酸三氟硼酸鉀鹽
英文關鍵詞: conjugate addition, rhodium, ketoester, boronic acid, potassium enol ether trifluoroborate
DOI URL: http://doi.org/10.6345/DIS.NTNU.DC.073.2018.B05
論文種類: 學術論文
相關次數: 點閱:119下載:0
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  • 本論文探討銠金屬與掌性雙環[2.2.1]雙烯配基形成之催化劑催化不對稱加成反應。內容分成下列兩部分。

    一、 一價銠金屬/掌性雙環[2.2.1]雙烯配基催化烯醇醚基三氟硼酸鉀鹽試劑對α,β-不飽和羰基化合物進行不對稱1,4-加成反應
    利用一價銠金屬以及掌性雙環[2.2.1]雙烯配基L1及L6形成之催化劑催化烯醇醚基三氟硼酸鉀鹽試劑2對環狀及鏈狀之α,β-不飽和羰基化合物1進行不對稱1,4-加成反應,可得到最高>99%之產率(13–>99%)及>99.5%之鏡像選擇性(44–>99.5% ee)的加成產物3。加成產物3ha可經由水解反應得到具有掌性中心之1,5-雙羰基結構23a,改善傳統由醛進行麥可加成反應(Michael addition)時會遇到加成產物為外消旋混合物;以及易有醛醇反應(aldol reaction)副反應發生之缺點。

    二、 銠金屬(I)/掌性雙環[2.2.1]雙烯配基催化芳基硼酸試劑對α-酮酯化合物進行不對稱1,2-加成反應:(S)-Flutriafol的合成
    利用一價銠金屬以及掌性雙環[2.2.1]雙烯配基L6形成之催化劑催化芳基硼酸試劑10對α-酮酯化合物76進行不對稱1,2-加成反應。僅需使用0.5 mol %之低催化量的一價銠金屬催化劑,即可得到最高達99%之鏡像選擇性(90–99% ee)及最高>99%之產率(2–>99%)的加成產物78,並成功建立具有掌性四級碳中心之α-羥基酯結構。此研究提供一個更快速、更簡單且產率更高的(S)-Flutriafol ((S)-90)新合成方法。

    This thesis describes the employment of chiral Rh(I)-catalysts, in situ generated from [RhCl(C2H4)2]2 and chiral bicyclo[2.2.1]heptadienes, in the enantioselective addition reactions. The content covers two parts.

    I. Enantioselective 1,4-Addition Reactions of Potassium Enol Ether Trifluoroborates to α,β-Unsaturated Carbonyl Compounds Catalyzed by Rh(I)/Chiral Bicyclo[2.2.1] dienes.
    An enantioselective 1,4-addition of potassium enol ether trifluoroborates 2 to α,β-unsaturated carbonyls is described. In the presence of 3.0 mol % of the catalysts generated in situ from the [RhCl(C2H4)2]2 pre-catalyst and diene L1 or L6, the asymmetric reaction afforded the desired adducts 3 in up to 99% yield (13–>99%) and with up to >99.5% ee (44–>99.5% ee). The method was applied to the synthesis of 1,5-dicarbonyl 23a via a microwave-assisted acid hydrolysis that overcomes those existed in the conventional addition of aldehydes to α,β-unsaturated carbonyl compounds.

    II. Enantioselective Arylation of α-Ketoesters: Total Synthesis of (S)-Flutriafol
    A highly enantioselective addition of arylboronic acids 10 to α-ketoesters 76 catalyzed by a Rh(I)-chiral diene catalyst is reported. This transformation proceeds regioselectively in the presence of as low as 0.5 mol % of the catalyst generated in situ from a Rh(I) salt and diene L6 to afford tertiary chiral α-hydroxy esters 78 with high stereoselectivities (90–99% ee) and in good chemical yields (2–>99%). The method provides a new, expeditious and enantioselective approach to the synthesis of the fungicide (S)-Flutriafol ((S)-90).

    中文摘要.……...i 英文摘要….…....iii 謝誌 ……...….v 縮寫對照表………....xvi 第一章 緒論......1 1-1 何謂鏡像異構物(Enantiomer)?......1 1-2 鏡像異構物(Enantiomer)的重要性......3 1-3 不對稱催化(asymmetric catalysis)合成的重要性......4 1-4 銠金屬催化不對稱芳基化反應(RCAA, Rhodium Catalyzed Asymmetric Arylation)......5 第二章 一價銠金屬/掌性雙環[2.2.1]雙烯配基催化烯醇醚基三氟硼酸鉀鹽試劑對α,β-不飽和羰基化合物進行不對稱1,4-加成反應.......12 2-1 文獻回顧......12 2-2 實驗設計與概念......23 2-3 實驗結果與討論......30 2-4 合成應用......57 第三章 銠金屬(I)/掌性雙環[2.2.1]雙烯配基催化芳基硼酸試劑對α-酮酯化合物進行不對稱1,2-加成反應:(S)-Flutriafol的合成…………………….58 3-1 文獻回顧......58 3-2 實驗結果與討論......68 3-3 合成應用......100 第四章 結論......105 第五章 實驗部分......107 分析儀器及基本實驗......107 General procedures for the synthesis of potassium enol ether trifluoroborates 2a–2f (Exemplified for 2a).......110 General Procedure for Rhodium-Catalyzed 1,4-Addition......116 General Procedures for the Synthesis of (R)-5-oxo-3,5-diphenyl-pentanal (23a)...........143 General Procedure for Rhodium-Catalyzed 1,2-Addition.......145 General Procedures for the Synthesis of (S)-Flutriafol ((S)-90).........184 參考文獻..................190

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