Author: |
林子洋 Lin, Zi-Yang |
---|---|
Thesis Title: |
利用一價銠金屬催化芳基硼酸對3號位具酯基之香豆素化合物進行不對稱1,4-加成反應 Enantioselective 1,4-Arylation of Coumarin-3-carboxylic Esters Using Rh(І)/Diene Catalysts |
Advisor: |
吳學亮
Wu, Hsyueh-Liang |
Degree: |
碩士 Master |
Department: |
化學系 Department of Chemistry |
Thesis Publication Year: | 2020 |
Academic Year: | 108 |
Language: | 中文 |
Number of pages: | 193 |
Keywords (in Chinese): | 銠金屬催化 、掌性雙烯配基 、1,4-加成反應 |
Keywords (in English): | Rh(Ⅰ)-catalyst, chiral diene ligand, 1,4-addition reaction |
DOI URL: | http://doi.org/10.6345/NTNU202001313 |
Thesis Type: | Academic thesis/ dissertation |
Reference times: | Clicks: 154 Downloads: 12 |
Share: |
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摘要
本論文敘述利用掌性雙環 [2.2.1] 雙烯配體L5a與一價銠金屬形成之催化劑催化芳基硼酸7與三號位具酯基取代之香豆素化合物24進行不對稱1,4-加成反應。此加成反應產生9−99%產率,鏡像超越值7−99%的加成產物25。此方法可以用於合成抗利尿藥物 (R)–Tolterodine (14)
Abstract
This thesis describes an asymmetric 1,4-conjugated addition reaction of arylboronic acids 7 to various coumarin-3-carboxylic esters 24 in the presence of 3.0 mol % Rh(Ⅰ)-catalyst consisting of chiral diene ligand L5a, affording adducts 25 in up to 99% yield, d.r > 20:1 and 99% ee. This asymmetric transformation demonstrates its usefulness in the synthesis of an anti-diuretic drug, (R)–Tolterodine (14)
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