一價銠金屬/雙環[2.2.1]雙烯配基催化烯醇醚基三氟硼酸鉀鹽與芳香基亞胺進行不對稱加成反應及藥物(S)-達伯西汀的合成應用 Rhodium/Chiral Diene-catalyzed Enantioselective Addition of Potassium Enol Ether Trifluoroborates to N-Tosyl Aldimines: Synthesis of (S)-Dapoxetine

dc.contributor 吳學亮 zh_TW
dc.contributor Wu, Hsyueh-Liang en_US
dc.contributor.author 黃普航 zh_TW
dc.contributor.author Huang, Pu-Hang en_US
dc.date.accessioned 2019-09-04T09:07:49Z
dc.date.available 不公開
dc.date.available 2019-09-04T09:07:49Z
dc.date.issued 2016
dc.description.abstract 本論文利用一價銠金屬與本實驗室開發之掌性雙環[2.2.1]雙烯配基L1e的催化系統,使各式烯醇醚基三氟硼酸鉀鹽試劑 53a‒f與芳香基亞胺10a‒o進行不對稱催化加成反應,在100 oC下以甲苯作為溶劑,添加100 wt%研磨過分子篩 (MS 4Å),反應六小時,可合成出具有高鏡像選擇性的新型掌性烯丙基胺骨架之產物34,其產率為21%到83%,鏡像超越值為94%到>99.5% ee。 在合成應用上,利用合成出的新型掌性烯丙基胺化合物34ae,經由簡單的官能基轉變,就可以合成出市售藥物 (S)-Dapoxetine (60)。 zh_TW
dc.description.abstract This thesis describes the asymmetric synthesis of optically active amines bearing enol ethers. In the presence of 5.0 mol% of the Rh(I) catalyst comprising chiral diene ligand L1e, the enantioselective addition of potassium enol ether trifluoroborates (53a‒f) to aldimines bearing N-Ts protecting groups afforded the desired allylic amines in 21– 83% yields with 94–>99.5% ee. The method was applied to the total synthesis of (S)-Dapoxetine (60). en_US
dc.description.sponsorship 化學系 zh_TW
dc.identifier G060342070S
dc.identifier.uri http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060342070S%22.&%22.id.&
dc.identifier.uri http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/100076
dc.language 中文
dc.subject 達伯西汀 zh_TW
dc.subject 一價銠金屬 zh_TW
dc.subject 三氟硼酸鉀鹽 zh_TW
dc.subject 掌性 zh_TW
dc.subject 烯丙基胺 zh_TW
dc.subject 不對稱催化 zh_TW
dc.subject Dapoxetine en_US
dc.subject Potassium trifluoroborates en_US
dc.subject allylic amine en_US
dc.subject Chiral en_US
dc.subject Rhodium en_US
dc.subject diene ligand en_US
dc.subject Enantioselective en_US
dc.title 一價銠金屬/雙環[2.2.1]雙烯配基催化烯醇醚基三氟硼酸鉀鹽與芳香基亞胺進行不對稱加成反應及藥物(S)-達伯西汀的合成應用 zh_TW
dc.title Rhodium/Chiral Diene-catalyzed Enantioselective Addition of Potassium Enol Ether Trifluoroborates to N-Tosyl Aldimines: Synthesis of (S)-Dapoxetine en_US
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