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The preparation of copper salt of this type of dicarboxylic acid was also\nstudied. Optically active 2,2\u0027-dihydroxy-1,1\u0027-binaphthalene-4,4\u0027-dicarboxylic acid 2a was\nprepared from the corresponding bromide 3 via cyanation followed by hydrolysis although\nthe reaction proceeded in very low yield. We found that 2a could be effectively prepared\nfrom 3 via palladium complex-catalyzed vinylation followed by KMnO4 oxidation. Direct\ncarboxylation of 3 via lithiation followed by the reaction with CO2 was unsuccessful because\nof the instability of the monolithiated intermediate. The synthesis of optically active\nallene-1,3-dicarboxylic acid 9 was investigated. The optical resolution of racemic 9 via the\nquinine salt was unsuccessful due to slow decomposition, therefore, diasteromeric\nresolution of (-)-menthyl ester was investigated. A copper (II) salt of racemic\n2,2\u0027-dihydroxy-1,1\u0027-binaphthalene-3,3\u0027-dicarboxylic acid 15 was prepared. X-ray\ncrystallographic analysis of the single crystal of 15-Cu (II) showed a 2D infinite sheet\nstructure, where each sheet was composed of only one of the enantiomers of 15. The\ncrystal had micropores of 4.15 Å diameter, which well corresponded to the value obtained\nfrom the micropore size distribution measurement. 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不斉ナノ空間の構築と不斉認識・不斉合成反応
http://hdl.handle.net/10487/5272
http://hdl.handle.net/10487/5272d107bcf4-f737-4229-8d5f-380c0d094a4d
名前 / ファイル | ライセンス | アクション |
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06 19 27-32.pdf (3.2 MB)
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Item type | 紀要論文 / Departmental Bulletin Paper(1) | |||||
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公開日 | 2009-12-21 | |||||
タイトル | ||||||
タイトル | 不斉ナノ空間の構築と不斉認識・不斉合成反応 | |||||
言語 | ||||||
言語 | jpn | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | axially chiral dicarboxylic acid | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | copper | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | chiral nano-space | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | open frame network | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | departmental bulletin paper | |||||
著者 |
木原, 伸浩
× 木原, 伸浩× Kihara, Nobuhiro× 森, 和亮× Mori, Wasuke |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | Synthesis of axially chiral dicarboxylic acids with a rigid and straight structure was studied. The preparation of copper salt of this type of dicarboxylic acid was also studied. Optically active 2,2'-dihydroxy-1,1'-binaphthalene-4,4'-dicarboxylic acid 2a was prepared from the corresponding bromide 3 via cyanation followed by hydrolysis although the reaction proceeded in very low yield. We found that 2a could be effectively prepared from 3 via palladium complex-catalyzed vinylation followed by KMnO4 oxidation. Direct carboxylation of 3 via lithiation followed by the reaction with CO2 was unsuccessful because of the instability of the monolithiated intermediate. The synthesis of optically active allene-1,3-dicarboxylic acid 9 was investigated. The optical resolution of racemic 9 via the quinine salt was unsuccessful due to slow decomposition, therefore, diasteromeric resolution of (-)-menthyl ester was investigated. A copper (II) salt of racemic 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylic acid 15 was prepared. X-ray crystallographic analysis of the single crystal of 15-Cu (II) showed a 2D infinite sheet structure, where each sheet was composed of only one of the enantiomers of 15. The crystal had micropores of 4.15 Å diameter, which well corresponded to the value obtained from the micropore size distribution measurement. Because of the micropore structure, the crystal showed a large surface area (BET: 642 m2g-1, Langmuire: 919 m2g-1). |
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内容記述 | ||||||
内容記述タイプ | Other | |||||
内容記述 | ■原 著■ 2007 年度神奈川大学総合理学研究所共同研究助成論文 | |||||
書誌情報 |
Science Journal of Kanagawa University 巻 19, p. 27-32, 発行日 2008-06-30 |
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ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 1880-0483 | |||||
書誌レコードID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AA12068302 | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
その他の言語のタイトル | ||||||
その他のタイトル | Construction of Chiral Nano-Space toward Chiral Recognition and Asymmetric Reaction | |||||
出版者 | ||||||
出版者 | 神奈川大学 |