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アミン触媒を用いるエノール化可能なケトンの官能基化
https://doi.org/10.15102/1394.00000171
https://doi.org/10.15102/1394.00000171f490e502-f4f3-4733-b5bc-d748437432c8
| 名前 / ファイル | ライセンス | アクション |
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Final Exam Abstract (42.9 kB)
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| Item type | 学位論文 / Thesis or Dissertation(1) | |||||||||
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| 公開日 | 2017-12-21 | |||||||||
| タイトル | ||||||||||
| タイトル | アミン触媒を用いるエノール化可能なケトンの官能基化 | |||||||||
| 言語 | ja | |||||||||
| タイトル | ||||||||||
| タイトル | Amine Catalyzed Functionalization of Enolizable Ketones | |||||||||
| 言語 | en | |||||||||
| 言語 | ||||||||||
| 言語 | eng | |||||||||
| 資源タイプ | ||||||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_db06 | |||||||||
| 資源タイプ | doctoral thesis | |||||||||
| ID登録 | ||||||||||
| ID登録 | 10.15102/1394.00000171 | |||||||||
| ID登録タイプ | JaLC | |||||||||
| アクセス権 | ||||||||||
| アクセス権 | open access | |||||||||
| アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||||||
| 著者 |
ザン, ドンシン
× ザン, ドンシン
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| 著者 (英) |
Zhang, Dongxin
× Zhang, Dongxin
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| 抄録 | ||||||||||
| 内容記述タイプ | Other | |||||||||
| 内容記述 | Development of efficient methods for the synthesis of biologically important molecules in safe, atom economical, and environmentally friendly ways is a significant goal of modern organic chemistry. In this thesis, efficient methods using amines as catalysts for functionalization of enolizable ketones and synthesis of potential biofunctional molecules have been developed. First, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was indentified to be an efficient catalyst for fast regioselective aldol reactions. Molecules containing tertiary alcohols were concisely obtained through the aldol reactions. The developed DBU-catalysis was applied for the synthesis of spirooxindoles and trifluoromethyl-substituted alcohols. Although the DBU-catalyzed aldol reactions are not enantioselective, the enantiomerically pure forms of the aldol products derived from β-keto esters were obtained by the resolution of the enamines of the aldol products with a homochiral amine. Second, deuteration studies were carried out to elucidate the mechanism of the regioselective formation of the products in the aldol reactions catalyzed by DBU and to understand the relationship between the carbanion formation and the bond-formation. Finally, enantioselective oxa-hetero-Diels-Alder reaction of enones with aryl trifluoromethyl ketones catalyzed by a novel amine catalyst system was developed. Tetrasubstituted carbon centers bearing a trifluoromethyl group were concisely constructed with the formation of the tetrahydropyranone ring. The hetero-Diels-Alder products were further transformed to various trifluoromethyl-substituted tetrahydropyran derivatives. | |||||||||
| 言語 | en | |||||||||
| 口頭試問日 | ||||||||||
| 値 | 2017-07-10 | |||||||||
| 学位授与年月日 | ||||||||||
| 学位授与年月日 | 2017-08-14 | |||||||||
| 学位名 | ||||||||||
| 学位名 | Doctor of Philosophy | |||||||||
| 学位授与番号 | ||||||||||
| 学位授与番号 | 甲第6号 | |||||||||
| 学位授与機関 | ||||||||||
| 学位授与機関識別子Scheme | kakenhi | |||||||||
| 学位授与機関識別子 | 38005 | |||||||||
| 学位授与機関名 | Okinawa Institute of Science and Technology Graduate University | |||||||||
| 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 | |||||||||
| 権利 | ||||||||||
| 権利情報 | © 2017 The Author | |||||||||
