一價銠金屬催化氮-對甲苯磺醯基之1,2‐二氫喹啉進行不對稱氫芳基化反應
| dc.contributor | 吳學亮 | zh_TW |
| dc.contributor | Wu, Hsyueh-Liang | en_US |
| dc.contributor.author | 黃思穎 | zh_TW |
| dc.contributor.author | Huang, Szu-Ying | en_US |
| dc.date.accessioned | 2020-10-19T06:51:10Z | |
| dc.date.available | 2025-04-01 | |
| dc.date.available | 2020-10-19T06:51:10Z | |
| dc.date.issued | 2020 | |
| dc.description.abstract | 本篇論文探討一價銠金屬試劑與掌性雙環[2.2.1]雙烯配基L2a形成之催化劑，於溫度100 ℃且使用環戊基甲基醚為溶劑，並加入甲醇為添加劑的條件下，催化1,2‐二氫喹啉或2H-色原烯12與四芳基硼鈉13進行不對稱加成反應，得到一系列3號位具芳香基之掌性1,2,3,4-四氫喹啉或3號位具芳香基之掌性色原烷14，產率為10–92%，鏡像超越值為87–99%。此外，利用掌性1,2,3,4-四氫喹啉化合物14mh進行去甲基反應及利用掌性1,2,3,4-四氫喹啉化合物14nn經由宮浦硼酸化 (Miyaura borylation)與氧化反應可合成目標產物雌激素乙型受體促效劑 ((R)-3)，前者產率為86%，後者兩個步驟的總產率為52%。 | zh_TW |
| dc.description.abstract | This thesis describes an enantioselective addition of sodium tetraarylborates 13 to 1,2-dihydroquinolines or 2H-chromenes 12 in cyclopentyl methyl ether at 100 ℃ with 5.0 equiv of methanol as an additive in the presence of 3.0 mol % of Rh(I)-catalyst in situ generated from the [RhCl(C2H4)2]2 and chiral bicyclo[2.2.1]heptadiene ligand L2a. The desired products 14 were generated in 10–92% yields with 87–99% ees. In addition, the synthesis of Estrogen receptor β agonist ((R)-3) was achieved by demethylation of compound 14mh in 86% yield. The desired product ((R)-3) was also obtained by Miyaura borylation of compound 14nn followed by oxidation in 52% yield for 2 steps. | en_US |
| dc.description.sponsorship | 化學系 | zh_TW |
| dc.identifier | G060742033S | |
| dc.identifier.uri | http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060742033S%22.&%22.id.& | |
| dc.identifier.uri | http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/111142 | |
| dc.language | 中文 | |
| dc.subject | 鏡像選擇性 | zh_TW |
| dc.subject | 一價銠金屬催化 | zh_TW |
| dc.subject | 氫芳基化反應 | zh_TW |
| dc.subject | 1,2‐二氫喹啉 | zh_TW |
| dc.subject | 2H-色原烯 | zh_TW |
| dc.subject | 四芳基硼鈉試劑 | zh_TW |
| dc.subject | 不對稱加成反應 | zh_TW |
| dc.subject | 掌性 | zh_TW |
| dc.subject | 掌性雙環[2.2.1]雙烯配基 | zh_TW |
| dc.subject | enantioselective | en_US |
| dc.subject | Rhodium(I)-catalyzed | en_US |
| dc.subject | hydroarylation | en_US |
| dc.subject | 1,2-dihydroquinolines | en_US |
| dc.subject | 2H-chromenes | en_US |
| dc.subject | sodium tetraarylborates | en_US |
| dc.subject | asymmetric addition | en_US |
| dc.subject | chiral | en_US |
| dc.subject | chiral bicyclo[2.2.1]diene ligands | en_US |
| dc.title | 一價銠金屬催化氮-對甲苯磺醯基之1,2‐二氫喹啉進行不對稱氫芳基化反應 | zh_TW |
| dc.title | Rhodium(I)-Catalyzed Asymmetric Hydroarylation of N-Tosyl 1,2-Dihydroquinolines | en_US |