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Asymmetric reduction using lithium aluminum hydride and borane modified by chiral ligands derived from (1R)-(-)- myrtenal
Authors
Shwu-Huey Wang
王淑慧
Publication date
6 June 2014
Publisher
化學學系
Abstract
鏡像選擇還原(enantioselective reduction)趨掌性 (pro- chiral) 酮 類化合物,生成具光學活性(optically active)的醇類化合物,在有機合 成是相當重要的。基於此,本論文利用(1R) -(-)-桃金娘苫烯醛( myrtenal)合成掌性配位基(chiral ligand)將他們作為四氫化鋁鋰 (lithium aluminum hydride) 及氫化硼 (boron hydride)之掌性修飾劑( modifier)對趨掌性酮類化合物進行不對稱還原反應之研究結果。首先, (1R)-(-)-桃金娘苫烯醛與乙二醇反應,將醛基保護後,再以四氧化鋨氧 化成雙羥基(dihydroxy)化合物 29 (57%)。將雙醇類化合物 29 之雙羥基 以丙酮保護,同時去除醛基保護後得到dioxalane 32 (92%)。 對化合物 32 進行還原胺化反應 (reductive amination)可以得到胺類化合物 33 (67%),最候將 dioxalane保護基,得到胺基雙醇掌性修飾劑 31 (95%)。 將化合物 29 之二級醇與碘甲烷反應產生甲醚化合物 34 (84%) ,將化合 物 34 醛基之保護去除而得到化合物 35 (74%)。再將醛基以還原胺化反 應轉變成胺基醇掌性修飾劑 26b (69%),將掌性修飾劑 26b 與甲基硼酸 進行環化反應,得到掌性催化劑 38b 。將掌性修飾劑 26b 作為四氫化鋁 鋰修飾劑,對乙醯苯(ace- tophenone)﹑丙醯苯(propiophenone)﹑丁醯 苯(butyrophenone)﹑ 乙酸苯酮(benzylacetone)﹑2-辛酮(2-octanone) 進行一系列還原反應,可得到相當好之化學產率(80100%)及普通之光學產 率 (316%)的掌性二級醇。將掌性催化劑 38b 與硼烷對上列酮類化合物進 行還原反應,可得到適可及不錯之化學產率(3581%)及普通之光學產 率(0.913%)的掌性二級醇
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National Chung Hsing University Institutional Repository
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Last time updated on 16/06/2016
National Chung Hsing University Institutional Repository
See this paper in CORE
Go to the repository landing page
Download from data provider
oai:ir.lib.nchu.edu.tw:11455/1...
Last time updated on 16/06/2016