- 學位論文
以不對稱有機催化進行夫里德耳-夸夫特烷基化反應：利用多電子酚類與烷基亞甲基假吲哚合成具掌性的吲哚衍生物
Organocatalytic Asymmetric Friedel-Crafts Alkylation through Electron-rich Phenols with Alkylideneindolenines: The Synthesis of Chiral Indole Derivatives
摘要
本文主要研究以不對稱有機催化進行夫里德耳-夸夫特烷基化反應（organocatalytic asymmetric Friedel-Crafts alkylation reaction），透過各種吲哚衍生物在鹼性條件下生成所需中間體：烷基亞甲基假吲哚（alkylideneindolenine），在（硫）脲取代的金雞納生物鹼雙功能有機催化劑 （（thio）urea- based cinchona alkaloid bifunctional organocatalyst）雙重活化引導下，使富含電子（electron-rich）的酚類，建構具有選擇性的三級碳、四級碳立體中心，同時得到具掌性的吲哚衍生物，並且在通用性測試上最高達到鏡像超越值97%與產率99%。
並列摘要
Abstract Our purpose is to develop the organocatalytic asymmetric Friedel-Crafts alkylation reaction of electron-rich phenols to alkylideneindolenines generated in situ from arenesulfonylalkylindoles. These reactions were catalyzed by (thio)urea- based cinchona alkaloid bifunctional organocatalysts, producing chiral indole derivatives in yields (up to 99%) and enantioselectivites (up to 97%).
參考文獻
第七章 參考文獻
1. Fahlbusch, K. G.; Hammerschmidt, F. J.; Panten, J.; Pickenhagen, W.; Schatkowski, D.; Bauer, K.; Garbe, D.; Surburg, H. Flavors and Fragrances. Ullmann's Encyclopediaof Industrial Chemistry; Wiley-VCH: Wiley Online Library, 2003.
2. Eriksson, T.; Björkman, S.; Höglund, P. Eur. J. Clin. PHarmacol. 2001, 57, 365-376.
3. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "stereoselective synthesis".
4. (a) Nakamura, K.; Yamanaka, R.; Matsuda, T.; Harada, T. Tetrahedron Asymmetry. 2003, 14, 2659-2681. (b) Masaru, W.; Michihiko, K.; Hiroshi, K.; Yoshihiko, Y.; Noriyuki, K.; Junzo H.; Sakayu, S. Biosci. Biotechnol. and Biochem., 1998, 62, 280-285. (c) Yasohara, Y.; Kizaki, N.; Hasegawa, J.; Takahashi, S.; Wada, M.; Kataoka, M.; Shimizu, S. Appl. Microbiol. Biotechnol., 1999, 51, 847–851. (d) Drienovská, V.; Rioz-Martínez, A.; Draksharapu, A.; Roelfes, G. Chem. Sci., 2015, 6, 770–776.
延伸閱讀
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- 蕭建基（2008）。利用鑭系金屬催化掩飾鄰苯醌與不對稱噁唑酮親雙烯劑進行分子間Diels-Alder反應之研究〔碩士論文，國立清華大學〕。華藝線上圖書館。https://doi.org/10.6843/NTHU.2008.00348
- 鄭竣丰（2013）。有機太陽能電池用―含5,6-雙氟-2,1,3-苯并噻二唑拉電子基與噻吩、呋喃及硒吩推電子基之共聚合物及其含紫質側鏈之共聚合物之合成與鑑定〔碩士論文，國立交通大學〕。華藝線上圖書館。https://doi.org/10.6842/NCTU.2013.00062
- 劉邦民（2010）。Catalytic Asymmetric α-Amination of Aldehydes and Ketones by Camphor-pyrrolidinyl Derived Organocatalysts〔博士論文，國立臺灣師範大學〕。華藝線上圖書館。https://www.airitilibrary.com/Article/Detail?DocID=U0021-1610201315204535
- Vagh, S. S. (2021). Asymmetric Catalysis for the Enantioselective Construction of Spirooxindole-Fused Cyclopenta[c]chromen-4-ones and Intramolecular Wittig Strategy towards the Synthesis of Diverse Heteroarenes [doctoral dissertation, National Taiwan Normal University]. Airiti Library. https://doi.org/10.6345/NTNU202100092